Sodium hydride → Ethyl 7-[(triisopropylsilyl)thio]chromane-2-carboxylate

HRID 39037

反応式

HRID 39037 の反応式
[H-].[Na+].[CH:3]([Si:6]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[SH:7])([CH3:5])[CH3:4].FC(F)(F)S(O[C:20]1[CH:29]=[C:28]2[C:23]([CH2:24][CH2:25][CH:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:27]2)=[CH:22][CH:21]=1)(=O)=O>C1(C)C=CC=CC=1.C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:11]([Si:6]([CH:3]([CH3:5])[CH3:4])([CH:8]([CH3:10])[CH3:9])[S:7][C:20]1[CH:29]=[C:28]2[C:23]([CH2:24][CH2:25][CH:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:27]2)=[CH:22][CH:21]=1)([CH3:13])[CH3:12]

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 86652954Ethyl 7-{[(trifluoromethyl)sulfonyl]oxy}chromane-2-carboxylate

生成物 1

HCID 66878159Ethyl 7-[(triisopropylsilyl)thio]chromane-2-carboxylate

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of NaH (1.02 g, 25.6 mmol, 60% in mineral oil) in toluene (60 ml) was added triisopropylsilanethiol (4.24 g, 22.3 mmol). After stirring at room temperature for 30 min, to the mixture were added a solution of ethyl 7-{[(trifluoromethyl)sulfonyl]oxy}chromane-2-carboxylate (6.07 g, 17.1 mmol) in THF (60 ml) and tetrakis(triphenylphosphine) palladium (0.39 g, 0.34 mmol), and the mixture was degassed under N2. After heating at 90° C. for 1.5 h under N2, the solvents were evaporated and the residue was purified by column chromatography (EtOAc/Isooctane) to afford the title compound. Yield: 6.84 g. MS m/z (rel. intensity, 70 eV) 394 (M+, 27), 277 (52), 352 (26), 351 (bp), 251 (50).

後処理

  1. customthe mixture was degassed under N2
  2. temperatureAfter heating at 90° C. for 1.5 h under N2
  3. customthe solvents were evaporated
  4. customthe residue was purified by column chromatography (EtOAc/Isooctane)

出典と根拠

ORDレコード
ord-4c6816f4fbd843908afe950dc79559d0
出典データセット
uspto-grants-2013_09
特許番号
US08524766B2

関連ノート

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