(3S)-3-benzyloxy-1,2-epoxybutane → (2S)-2-benzyloxy-6-phenylhexan-3-ol

Reaction equation

[CH2:1]([O:8][C@@H:9]([CH3:13])[CH:10]1[O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([Mg]Cl)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:1]([O:8][C@H:9]([CH:10]([OH:12])[CH2:11][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 57223577(3S)-3-benzyloxy-1,2-epoxybutane

HCID 178418865HCID 178418865, compound

Product 1

HCID 57074659(2S)-2-benzyloxy-6-phenylhexan-3-ol

Procedure

(2S)-2-benzyloxy-6-phenylhexan-3-ol was prepared from (3S)-3-benzyloxy-1,2-epoxybutane (obtained in Preparation 9) and phenethylmagnesium chloride.

Sources & evidence

ORD record: ord-3b209fff08b3464c8bb441a9aecd06d7
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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