Formic Acid → 3-Hydroxy-3-(thiophen-2-yl)propanenitrile

HRID 2120005

反応式

HRID 2120005 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[CH2:7][C:8]#[N:9].C(N(CC)CC)C.C(O)=O>CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.[Cl-].[Ru+2].O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:10])[CH2:7][C:8]#[N:9]

参加物

6

反応物 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 1418532-Thenoylacetonitrile

生成物 1

HCID 112521213-Hydroxy-3-(thiophen-2-yl)propanenitrile収率 92%

試薬・触媒・溶媒 2

HCID 11549108HCID 11549108、化合物触媒HCID 962Water溶媒

実験手順

A 50 ml Schlenk flask was charged with 4.54 g (30.0 mmol) of 3-(2-thienyl)-3-oxopropanenitrile, 10.88 ml (78 mmol) of triethylamine, 3.51 ml (93 mmol) of formic acid, and 19.1 mg (0.03 mmol, S/C=1000) of RuCl[(S,S)-Tsdpen](p-cymene) under an atmosphere of argon, and stirring was carried out at 30° C. for 24 hours. The reaction solution was poured into water and extracted with ether, and the organic layer was washed with saturated brine and then dried with anhydrous sodium sulfate. After removing the drying agent, the solvent was distilled off, and the oil so obtained was purified by silica gel column chromatography (eluant; n-hexane:ethyl acetate=4:1) to give 4.23 g of optically active 3-(2-thienyl)-3-hydroxypropanenitrile. 1H-NMR supported it was the target product and the yield was 92%.

後処理

  1. extractionextracted with ether
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. customAfter removing the drying agent
  5. distillationthe solvent was distilled off
  6. customthe oil so obtained
  7. customwas purified by silica gel column chromatography (eluant; n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-a684163af2534d949e713993e2a509cf
出典データセット
uspto-grants-2004_02
特許番号
US06686505B2

関連ノート

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