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

HRID 538026

反応式

HRID 538026 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichloride触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c9dcf23af0394fac92a90f9daae75d61
出典データセット
uspto-grants-2014_10
特許番号
US08865706B2

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