Sodium hydride → 4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

HRID 1466839

反応式

HRID 1466839 の反応式
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:20][C:18](=[O:19])[C:17]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:15]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:16]=1)[CH3:22]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 14945865Ethyl 3-bromo-4-methylbenzoate

生成物 1

HCID 667648104-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a 0° C. stirred solution of triisopropylsilanethiol (14.28 mmol, 3.07 mL) in THF was added sodium hydride (14.28 mmol, 0.57 g of a 60 wt % dispersion in mineral oil). After 30 min, the mixture was added to a solution of ethyl 3-bromo-4-methylbenzoate (10.99 mmol, 2.67 g) at room temperature, followed by tetrakis(triphenylphosphine)palladium(0) (0.55 mmol, 0.64 g). The resulting mixture was warmed to reflux and stirred for 18 hours, then cooled to room temperature and subjected to standard aqueous workup to afford the title compound which was used crude in the next step.

後処理

  1. temperatureThe resulting mixture was warmed
  2. temperatureto reflux

出典と根拠

ORDレコード
ord-75ea47a9512449939a7d3f0375b27f6f
出典データセット
uspto-grants-2015_04
特許番号
US09000025B2

関連ノート

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