Pyridine → 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

HRID 1269362

反応式

HRID 1269362 の反応式
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC(Cl)(O[C:21](=[O:27])[O:22][C:23](Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[CH3:35][S:36]([C:39]1[CH:44]=[CH:43][C:42](/[C:45](=[C:48](\[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)/[CH2:49][OH:50])/CO)=[CH:41][CH:40]=1)(=[O:38])=[O:37]>C(Cl)Cl>[C:21](=[O:27])([O:22][CH2:23]/[C:45](/[C:42]1[CH:41]=[CH:40][C:39]([S:36]([CH3:35])(=[O:38])=[O:37])=[CH:44][CH:43]=1)=[C:48](/[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)\[CH2:49][OH:50])[O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:11]=1

参加物

6

反応物 4

HCID 1049Pyridine2 回HCID 94429TriphosgeneHCID 149405563-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenolHCID 57434773(2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol

生成物 1

HCID 588411703-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate収率 42.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3.06 g of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenol and 1.50 g of triphosgene in 20 mL of CH2Cl2 cooled at −78° C. was added 1.2 mL of pyridine. The reaction mixture was warmed to rt. After 15–30 min, the white suspension was transferred to a solution containing 5.95 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and 1.5 mL of pyridine in 20 mL of CH2Cl2 at rt. The reaction was stirred at rt for 15 min. The reaction was quenched with aqueous 1N HCl, extracted with EtOAc and washed with brine, dried over sodium sulfate, evaporated, and purified by flash chromatography (50–70% EtOAc/hexane) to afford 1.26 g of the title compound as a yellow oil.

後処理

  1. waitAfter 15–30 min
  2. customThe reaction was quenched with aqueous 1N HCl
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. custompurified by flash chromatography (50–70% EtOAc/hexane)

出典と根拠

ORDレコード
ord-6194b3a9f7d34c66af83ac79ba135f51
出典データセット
uspto-grants-2007_04
特許番号
US07199154B2

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