三丁基膦 → methyl [(3S)-6-({4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

HRID 1908910笔记

反应方程式

HRID 1908910 反应方程式
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1.[O:16]=[S:17]1(=[O:40])[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:29]=[C:28]([CH3:30])[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37]O)[CH:32]=3)=[C:26]([CH3:39])[CH:25]=2)[CH2:19][CH2:18]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[O:16]=[S:17]1(=[O:40])[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:29]=[C:28]([CH3:30])[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][O:1][C:2]4[CH:15]=[CH:14][C:5]5[C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=5[CH:3]=4)[CH:32]=3)=[C:26]([CH3:39])[CH:25]=2)[CH2:19][CH2:18]1

参与物

7

反应物 4

HCID 13831三丁基膦HCID 73042偶氮二甲酰二哌啶HCID 53393313(S)2,3-二氢-6-羟基-3-香豆酮乙酸甲酯HCID 59342608{4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methanol

产物 1

HCID 59342604methyl [(3S)-6-({4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate收率 79%

试剂、催化剂与溶剂 2

HCID 1140甲苯溶剂HCID 8058正己烷溶剂

实验过程

A solution of methyl [(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate (0.208 g, 1.00 mmol), {4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.360 g, 1.00 mmol) and tributylphosphine (0.324 g, 1.60 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.404 g, 1.60 mmol) was added, and the mixture was stirred at room temperature for 3 hr under nitrogen atmosphere. Hexane (8 mL) was added to the reaction mixture, the precipitated insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30) to give the title compound (0.432 g, yield 79%) as a colorless oil.

后处理

  1. filtrationthe precipitated insoluble substance was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30)

来源与证据

ORD记录
ord-6dc9176240d34722b1060563cfc5d5e6
来源数据集
uspto-grants-2013_12
专利号
US08598226B2

反应笔记

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