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

HRID 493092

반응식

HRID 493092 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 4285986Bis[2-(diphenylphosphino)phenyl] ether촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
160 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b2416be841294e798e23e6aab34f8d16
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534791B2

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