Water → HCID 20040861, compound

HRID 1762454Notes

Reaction equation

B(Br)(Br)[Br:2].S(O[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([O:24]C)=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1([C:27]1[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=1)[CH3:26])(C)(=O)=O.O>C(Cl)Cl>[Br:2][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:24])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[CH3:26]

Participants

Conditions

Temperature: -60 °C

Procedure

A molar solution of boron tribromide in methylene chloride (27.6 ml.) was added to a stirred solution of (1RS,2RS)-1,2,3,4-tetrahydro-1-(4-mesyloxybutyl)-6-methoxy-2-p-methoxyphenyl-2-methylnaphthalene (Example 1; 2.3 g.) in methylene chloride (30 ml.) which was cooled to -60° C. under an atmosphere of argon, and the mixture was allowed to warm up to laboratory temperature and then poured into iced water. The mixture was extracted with ethyl acetate and the extract was dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 9:1 v/v mixture of toluene and ethyl acetate as eluent. There were thus separately obtained the (1RS, 2RS)- and (1RS,2SR)-isomers of 1-(4-bromobutyl)-2-p-hydroxyphenyl- 2-methyl-1,2,3,4-tetrahydronaphth-6-ol.

Workup

temperatureto warm up to laboratory temperature
extractionThe mixture was extracted with ethyl acetate
customthe extract was dried
customevaporated to dryness
customThe residue was purified by chromatography on a silica gel column
additiona 9:1 v/v mixture of toluene and ethyl acetate as eluent

Sources & evidence

ORD record: ord-94abdbc1f3894234bb4684a97cf65387
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04833135

Reaction notes

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