Phenethyl bromide → (3S,4S)-4-(tert-butyldimethylsilyloxy)-1-phenylpentan-3-ol

HRID 278485Notes

Reaction equation

[Si:1]([O:8][C@@H:9]([CH3:12])[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:13]1([CH2:19][CH2:20]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[Si:1]([O:8][C@H:9]([C@@H:10]([OH:11])[CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 7666Phenethyl bromide

HCID 10954305(2S)-2-[(tert-butyldimethylsilyl)oxy]propanal

Product 1

HCID 57308546(3S,4S)-4-(tert-butyldimethylsilyloxy)-1-phenylpentan-3-ol

Procedure

(2S,3S)-2-(tert-butyldimethylsilyloxy)-5-phenyl-pentan-3-ol was prepared from (S)-2-(tert-butyldimethylsilyloxy)propanal (Synthesis 1996, 652, 3.00 g) and 2-phenylethyl bromide.

Sources & evidence

ORD record: ord-c41a0839434d45489edad8878a8b2c81
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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