Methyl Acrylate → methyl (2E,5R)-6-(benzyloxy)-5-(2,2-diethoxyethoxy)hex-2-enoate

HRID 538026

반응식

HRID 538026 반응식
[CH2:1]([O:3][CH:4]([O:20][CH2:21][CH3:22])[CH2:5][O:6][C@H:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].[C:23]([O:27][CH3:28])(=[O:26])C=C>ClCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH2:10]([O:9][CH2:8][C@H:7]([O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:20][CH2:21][CH3:22])[CH2:17]/[CH:18]=[CH:19]/[C:23]([O:27][CH3:28])=[O:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 2

HCID 7294Methyl AcrylateHCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene

생성물 1

HCID 86729528methyl (2E,5R)-6-(benzyloxy)-5-(2,2-diethoxyethoxy)hex-2-enoate

시약·촉매·용매 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichloride촉매HCID 6344Dichloromethane용매

실험 절차

This reaction was carried out in 10 batches. To a solution of C2 (10 g, 32 mmol) in dichloromethane (400 mL) was added [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (Grubbs 2nd-generation catalyst, 1.38 g, 1.62 mmol) and methyl prop-2-enoate (69.7 g, 0.81 mol), and the reaction mixture was stirred at room temperature for 18 hours. Solvent was removed in vacuo, and the residue was purified via silica gel chromatography (Eluent: 3:1 petroleum ether/ethyl acetate) to provide the product as a yellow oil. Combined yield: 70 g, 0.19 mol, 59%. 1H NMR (400 MHz, CDCl3) δ 7.27-7.38 (m, 5H), 6.94-7.04 (m, 1H), 5.89 (br d, J=15.6 Hz, 1H), 4.58 (dd, J=5.3, 5.0 Hz, 1H), 4.54 (s, 2H), 3.73 (s, 3H), 3.44-3.7 (m, 9H), 2.41-2.55 (m, 2H), 1.21 (t, J=7.0 Hz, 3H), 1.20 (t, J=7.0 Hz, 3H).

후처리

  1. customSolvent was removed in vacuo
  2. customthe residue was purified via silica gel chromatography (Eluent: 3:1 petroleum ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-c9dcf23af0394fac92a90f9daae75d61
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865706B2

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