Aluminium lithium hydride → (R)-5-((tert-butyldiphenylsilyl)oxy)hexan-1-ol

HRID 921159Notes

Reaction equation

[Si:1]([O:18][C@H:19]([CH3:28])[CH2:20][CH2:21][CH2:22][C:23](OCC)=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:18][C@H:19]([CH3:28])[CH2:20][CH2:21][CH2:22][CH2:23][OH:24])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R)-ethyl 5-((tert-butyldiphenylsilyl)oxy)hexanoate (10 g, 25.09 mmol) in THF (150 mL) at 0° C. was added dropwise 1M LAH in THF (31.4 mL, 31.4 mmol) and the resulting mixture was stirred for 30 min. at 0° C. and then 2 h at room temp. The reaction was quenched with 1 mL of water (stir for 10 min), 1 mL of 15% NaOH/water (stir for 10 min), and then 2 mL of water. After stirring for 1 h, the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried under high vacuum for 16 h to afford (R)-5-((tert-butyldiphenylsilyl)oxy)hexan-1-ol (8.9 g, 24.96 mmol, 99% yield) as a clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.72-7.67 (m, 4H), 7.50-7.36 (m, 6H), 3.92-3.84 (m, 1H), 3.61-3.50 (m, 2H), 1.55-1.41 (m, 4H), 1.37-1.31 (m, 2H), 1.21-1.15 (m, 1H), 1.11-1.09 (m, 3H), 1.08 (s, 9H).

Workup

custom2 h
customat room temp
customThe reaction was quenched with 1 mL of water (stir for 10 min), 1 mL of 15% NaOH/water (stir for 10 min)
stirringAfter stirring for 1 h
filtrationthe mixture was filtered through celite
concentrationThe filtrate was concentrated in vacuo
customThe residue was dried under high vacuum for 16 h

Sources & evidence

ORD record: ord-c9fb7895cb4347b889a5326d2af82728
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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