Cesium carbonate → Methyl 4-{(4E)-5-[2-(4-chlorobutoxy)phenyl]-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate

HRID 1512214Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1/[CH:20]=[CH:21]/[CH:22]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([O:44][CH3:45])=[O:43])=[CH:38][CH:37]=1)[CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1/[CH:20]=[CH:21]/[CH:22]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][CH:41]=1)[CH2:23][CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.54 g (9.0 mmol) of 1-bromo-4-chlorobutane [CAS Reg. No. 6940-78-9] and 7.33 g (22.5 mmol) of anhydrous cesium carbonate are added to a solution of 1.0 g (2.25 mmol) of methyl 4-{(4E)-5-(2-hydroxyphenyl)-3-[4-(methoxycarbonyl)benzyl]pent-4-en-1-yl}benzoate (racemate; Example 18A) in 15 ml of dry toluene, and the mixture is then stirred at 60° C. for 18 h. The mixture is then filtered, and the filtrate is evaporated to dryness. The crude product obtained is taken up in ethyl acetate and washed twice with saturated sodium bicarbonate solution, and the organic phase dried over sodium sulfate and concentrated. The crude product is then purified by flash chromatography on silica gel (mobile phase: dichloromethane). This gives 0.850 g (1.59 mmol, 70.6% of theory) of a colorless oil.

Workup

filtrationThe mixture is then filtered
customthe filtrate is evaporated to dryness

Sources & evidence

ORD record: ord-1664e349ac4a4e4b89ff1385c231285f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217063B2

Reaction notes

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