HCID 20637669, compound → HCID 53740996, compound

HRID 1068056Notes

Reaction equation

HRID 1068056 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[O:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][Li]>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@@H:13]([OH:15])[CH2:14][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 20637669HCID 20637669, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 53740996HCID 53740996, compound

Procedure

(R)-6-Benzyloxyhex-1-ene oxide was prepared by copper catalyzed addition of 3-benzyloxypropyl-1-magnesium bromide to R-epichlorohydrin to form R-1-chloro-6-benzyloxyhexan-2-ol, which was then ring closed under basic conditions to (R)-6-benzyloxyhex-1-ene oxide. This epoxide was then treated with methyl lithium (1.5 M in diethyl ether) in the presence of dilithiotetrachlorocuprate (0.02 molar equivalents, 0.1 M in tetrahydrofuran) to yield (S)-1-benzyloxy-5-hydroxyheptane.

Sources & evidence

ORD record
ord-c2605316f88e4e77b4fa59e178d993e8
Source dataset
uspto-grants-2001_06
Patent number
US06248889B1

Reaction notes

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