Water → HCID 59210614, compound

HRID 2243297Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., 140 mg (0.51 mmol) of phosphorus tribromide were added to a solution of 500 mg (1.14 mmol) of methyl 8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-hydroxyoctanoate XVI in 5 ml of diethyl ether. The mixture was stirred at 0° C. for 1 h and at room temperature for another 16 h. Water was added, the mixture was extracted with cyclohexane and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, cyclohexane(ethyl acetate 10:1).

Workup

extractionthe mixture was extracted with cyclohexane
dry with materialthe combined organic phases were dried over Na2SO4
customThe product was purified chromatographically (silica gel, cyclohexane(ethyl acetate 10:1)

Sources & evidence

ORD record: ord-840976bf98674ed9866c62232acee50b
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674825B2

Reaction notes

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