(3S)-3-benzyloxy-1,2-epoxybutane → (2S)-2-benzyloxy-5-(1-naphthyl)pentan-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.[C:14]1([CH2:24][Mg]Cl)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>>[CH2:1]([O:8][C@H:9]([CH:10]([OH:12])[CH2:11][CH2:24][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=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 178478993HCID 178478993, compound

Product 1

HCID 57192398(2S)-2-benzyloxy-5-(1-naphthyl)pentan-3-ol

Procedure

(2S)-2-benzyloxy-5-(1-naphthyl)pentan-3-ol was prepared from (3S)-3-benzyloxy-1,2-epoxybutane (obtained in Preparation 9) and 1-naphthylmethylmagnesium chloride (J. Am. Chem. Soc. 1943, 65, 295).

Sources & evidence

ORD record: ord-33e6cca0da904967b72518ad71821d70
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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