Water → ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate

HRID 1267481ノート

反応式

HRID 1267481 の反応式
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH2:36][CH2:37][C:38]([F:50])([F:49])[C:39]([F:48])([F:47])[C:40]([F:46])([F:45])[C:41]([F:44])([F:43])[F:42])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH2:36][CH2:37][C:38]([F:50])([F:49])[C:39]([F:47])([F:48])[C:40]([F:45])([F:46])[C:41]([F:42])([F:43])[F:44])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:8]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)([CH3:13])[CH2:9][S:10]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 18546296ethyl 10-[(3RS,4RS)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate

生成物 1

HCID 18546293ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of ethyl 10-[(3RS,4RS)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (0.5 g, 0.67 mmol) in dichloromethane (10 mL) was cooled to −78° C. To this solution, a solution of boron tribromide in dichloromethane (1M, 5.37 ml) was slowly added dropwise, and the resulting mixture was stirred for 1 hour. The reaction vessel was then transferred to an ice-bath and the reaction mixture was further stirred for 3 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted with dichloromethane and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give ethyl 10-[(3RS,4RS)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)decanoate (0.4 g, Yield 84%) as a foam.

後処理

  1. customThe reaction vessel was then transferred to an ice-bath
  2. stirringthe reaction mixture was further stirred for 3 hours
  3. extractionwas then extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20/1)

出典と根拠

ORDレコード
ord-b1b35c41b3ca434bb8cb5d7fa0f5661d
出典データセット
uspto-grants-2003_04
特許番号
US06552069B1

反応ノート

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