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

HRID 985478ノート

反応式

HRID 985478 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+].[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]

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 131017693-Iodophenyl acetateHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ff458401309d4f08a5fd876cd4e86c76
出典データセット
uspto-grants-2005_03
特許番号
US06872730B2

反応ノート

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