Water → HCID 53740780, compound

HRID 2106670Notes

Reaction equation

[CH:1]1([C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH3:19])([C:6]2[S:7][CH:8]=[CH:9][C:10]=2[CH3:11])O)[CH2:3][CH2:2]1.[Br:20][Si](C)(C)C.O>ClCCl>[Br:20][CH2:3][CH2:2][CH:1]=[C:4]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[CH3:19])[C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH3:11]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of cyclopropyl(2,4-dimethylphenyl)(3-methyl-2-thienyl)methanol (7.0 g, 0.026 mole; obtained by the method described in Example 7) in dichloromethane (125 ml) was cooled to 10° C. and bromotrimethylsilane (4.0 g, 0.026 mole) in dichloromethane (50 ml) was added dropwise keeping the temperature at about 10° C. When addition was complete, water was added (250 ml) and the phases were separated. The aqueous phase was extracted with dichloromethane (25 ml). The combined organic phases was washed with a saturated sodium bicarbonate solution, brine and dried over sodium sulphate. The solvent was removed in vacuo leaving 1-bromo-4-(2,4-dimethylphenyl)-4-(3-methyl-2-thienyl)but-3-ene (8.7 g) as an oil. This bromide was converted by the method described in Example 7 into the title acid hydrochloride, M.p.=200°-201° C. (i-Propanol).

Workup

customobtained by the method
customat about 10° C
additionWhen addition
customthe phases were separated
extractionThe aqueous phase was extracted with dichloromethane (25 ml)
washThe combined organic phases was washed with a saturated sodium bicarbonate solution, brine
dry with materialdried over sodium sulphate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-cf2199a53588429384a98e2edaef9570
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04931450

Reaction notes

Loading…