Borane → HCID 15097577, compound

HRID 1651254Notes

Reaction equation

HRID 1651254 reaction equation
[C:1]([C:6](=[C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH2:7][C:8](O)=[O:9])([O:3][CH2:4][CH3:5])=[O:2].B>O1CCCC1>[CH2:4]([O:3][C:1](=[O:2])[C:6]([CH2:7][CH2:8][OH:9])=[C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH3:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 23051607HCID 23051607, compound

Product 1

HCID 15097577HCID 15097577, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

As described in Example 135, a solution of 3-carboethoxy-4,4-bis(3-methoxyphenyl)-3-butenoic acid (20.5 g) in dry tetrahydrofuran (100 mL) was treated with a solution of 1M borane in tetrahydrofuran (57 mL) and the reaction was stirred at room temperature overnight. After the usual work up, the crude product was purified by HPLC (diethyl etherhexane; 65:35) to provide 15.4 g of 2-hydroxyethyl-3,3-bis(3-methoxyphenyl)-2-propenoic acid ethyl ester, mp 102.5°-103.5° C. Anal. Calcd for C19H20O3 : C, 77.00; H, 6.80 Found: C, 77.12; H, 6.69

Workup

  1. customAfter the usual work up, the crude product was purified by HPLC (diethyl etherhexane; 65:35)

Sources & evidence

ORD record
ord-77f40ba2a57a43afb8ea644b4d502ad8
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

Loading…