KBS15-6 - Reduction of ferrocenyl methyl ester

[KlementineJBS]

Link to HIRAC and master page.

Last attempt was #15.

Ferrocenylmethanol synthesis .docx

Reaction Scheme

Outcome

354 mg (1.64 mmol), 104% - traces of ethyl acetate but ready to carry through.

Notes

N/A

[KlementineJBS]

22.07.22

1. Put a dry 50 mL 3 neck flask under nitrogen

2. Added 385 mg KBS14 (1.58 mmol) via solution transfer (dry THF)

3. Added LiAlH4 (1.0 M in THF, 2 mL, 2 mmol) on ice

4. Left stirring from 11 am

5. Quenched with ethyl acetate (15 mL) at 2 pm (TLC indicated completion - ignore SM spot as wrong SM was used)

6. Added Rochelle's salts to coordinate Al (40 mL)

7. Extracted once with ethyl acetate (25 mL). Noticed aqueous layer was milky, so put aside and added extra Rochelle's salts (30 mL) and left to stir. With sufficient Rochelle's salts, the aqueous should go clear as all the Al is coordinated.

8. Extracted again with ethyl acetate (2 x 40 mL)

9. Rotovapped down

Empty vial: 15.7755 Full vial: 16.1299 Mass: 354.4 mg

[KlementineJBS]

25.07.22

H NMR

Indicates that material is largely product, not SM.

1H NMR (300 MHz, CDCl3) δ 4.32 (2H), 4.24 (2H), 4.18 (5H), 4.16 (2H).

KBS15-6 cr_1.zip