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

HRID 2120005

반응식

HRID 2120005 반응식
[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]

참가 물질

6

반응물 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 1418532-Thenoylacetonitrile

생성물 1

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

시약·촉매·용매 2

HCID 11549108HCID 11549108, 화합물촉매HCID 962Water용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-a684163af2534d949e713993e2a509cf
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06686505B2

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