HCID 20305769, compound → HCID 20305765, compound

HRID 1732257Notes

Reaction equation

[O:1]([CH2:19][CH:20]([CH3:35])[CH2:21][CH2:22][CH2:23][C:24]([CH:27]1[O:31][C:30]([CH2:33][Br:34])([OH:32])[CH2:29][CH2:28]1)([OH:26])[CH3:25])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:36](OCC(C)CCCC(C1OC(CBr)(OC)CC1)(O)C)C1C=CC=CC=1>>[O:1]([CH2:19][CH:20]([CH3:35])[CH2:21][CH2:22][CH2:23][C:24]([CH:27]1[O:31][C:30]([CH2:33][Br:34])([O:32][CH3:36])[CH2:29][CH2:28]1)([OH:26])[CH3:25])[Si:2]([C:15]([CH3:18])([CH3:16])[CH3:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 20305769HCID 20305769, compound

HCID 20305770HCID 20305770, compound

Product 1

HCID 20305765HCID 20305765, compound

Procedure

7-t-Butyldiphenylsiloxy-2-[2-bromomethyl-2-methoxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol is prepared as a mixture of cis:trans isomers by employing 7-t-butyldiphenylsiloxy-2-[2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol (1.33 g) in place of 7-benzyloxy-2-(2-bromomethyl-2-hydroxy-tetrahydrofuran-5-yl)-6-methyl-heptan-2-ol in the process for the preparation of 7-benzyloxy-2-[2-bromomethyl-2-methoxy-tetrahydrofuran-5-yl]-6-methyl-heptan-2-ol. The mixture of cis and trans isomers is separated by chromatography on silica gel (ethyl acetate:hexane gradient) to give the cis isomer as a yellow oil (0.324 g) and then the trans isomer as a yellow oil (0.151 g):

Workup

additionThe mixture of cis and trans isomers
customis separated by chromatography on silica gel (ethyl acetate:hexane gradient)

Sources & evidence

ORD record: ord-4d80ecea91f64e288a873f7cdd67f2f8
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237055

Reaction notes

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