Sodium hydride → 3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate

HRID 985478노트

반응식

HRID 985478 반응식
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].[H][H].[C:16]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1)(=[O:18])[CH3:17]>C1COCC1.C1(C)C=CC=CC=1.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>[C:16]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:21]=1)(=[O:18])[CH3:17]

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 131017693-Iodophenyl acetateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 112210453-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate수율 52.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

Triisopropylsilanethiol (2.91 ml, 13.5 mmol) was added dropwise to a suspension of sodium hydride (325 mg, 13.5 mmol) in THF (10 ml). After the evolution of hydrogen ceased, a solution of 3-iodophenyl acetate (2.37 g, 9.0 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.04 g, 0.9 mmol) in toluene (90 ml) was added. After refluxing for 16 h under argon, the reaction was cooled to room temperature and the solvent was evaporated under vacuum. The resulting residue was dissolved in ethyl acetate, washed with 1N NaOH and brine, dried with sodium sulfate, filtered, and evaporated under vacuum. The crude product was chomatrographed over silica gel to yield 1.53 g (52%) of 3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate. NMR 1H Cl3CD δ: 7.34 (m, 2H), 7.23 (t, 1H, J=2.4 Hz), 6.94 (dd, 1H, J=1.2, 8.4 Hz), 2.28 (s, 3H), 1.25 (m, 3H), 1.08 (d, 18 H, J=7.2 Hz).

후처리

  1. temperatureAfter refluxing for 16 h under argon
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH and brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-ff458401309d4f08a5fd876cd4e86c76
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872730B2

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