Tris(propan-2-yl)silanethiol → Methyl-(2-triisopropylsilanylsulfanyl-benzyl)-carbamic acid tert-butyl ester

HRID 493092

反応式

HRID 493092 の反応式
[C:1]([O:5][C:6](=[O:17])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1I)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH:24]([Si:27]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[SH:28])([CH3:26])[CH3:25]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[N:7]([CH3:8])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:28][Si:27]([CH:29]([CH3:31])[CH3:30])([CH:32]([CH3:34])[CH3:33])[CH:24]([CH3:25])[CH3:26])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 3435097Tris(propan-2-yl)silanethiolHCID 23676156Sodium t-butoxideHCID 67018447tert-Butyl 2-iodobenzyl(methyl)carbamate

生成物 1

HCID 67018449Methyl-(2-triisopropylsilanylsulfanyl-benzyl)-carbamic acid tert-butyl ester収率 387%

試薬・触媒・溶媒 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] ether触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
160 °C

実験手順

(2-Iodo-benzyl)-methyl-carbamic acid tert-butyl ester (3.0 g, 8.64 mmol), tris(dibenzylideneacetone)dipalladium (0) (79 mg, 0.086 mmol), bis(2-diphenylphosphinophenyl)ether (93 mg, 0.17 mmol), sodium tert-butoxide (1.10 g, 11.2 mmol), triisopropylsilanethiol (1.73 g, 9.07 mmol) and dry toluene (15 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 160° C. for 15 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (1:4). This procedure is repeated an additional 3 times to furnish a total of 13.7 g (97%) of the title compound as an oil which is used in the next step without further purification.

後処理

  1. customThe reaction vessel is sealed
  2. temperatureUpon cooling the mixture
  3. additionis poured onto a plug of silica
  4. washthe product is eluted with ethyl acetate-heptane (1:4)

出典と根拠

ORDレコード
ord-b2416be841294e798e23e6aab34f8d16
出典データセット
uspto-grants-2009_05
特許番号
US07534791B2

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