Cesium carbonate → Ethyl (3S,4E)-3-(4-(((2'-(butyloxy)-6-(1,1-dimethylethyl)-5'-(methyloxy)-1,1'-biphenyl-3-yl)methyl)oxy)phenyl)-4-hexenoate

HRID 2101760Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8](/[CH:15]=[CH:16]/[CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[C:31]1[CH:36]=[C:35]([CH2:37]Cl)[CH:34]=[CH:33][C:32]=1[C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[C:31]1[C:32]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:33][CH:34]=[C:35]([CH2:37][O:1][C:2]2[CH:3]=[CH:4][C:5]([C@H:8](/[CH:15]=[CH:16]/[CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)[CH:36]=1)[CH2:19][CH2:20][CH3:21]

Participants

Conditions

Temperature: 23 °C

Procedure

A mixture of compound B (11 mg, 47 μmol), compound C (17 mg, 47 μmol), and cesium carbonate (23 mg, 70 μmol) in DMF (1.0 mL) was stirred for 16 hours at 23° C. The mixture was diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound 11.1 (21 mg, 81% yield) as a colorless oil. MS ESI (pos.) m/e: 576 (M+H2O), 581 (M+Na).

Workup

washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

Sources & evidence

ORD record: ord-db516d52d7f7448496d0771ec1358fb2
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572934B2

Reaction notes

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