Tetrahydrofuran → 4-Phenylbut-3-en-2-ol

HRID 467283

반응식

HRID 467283 반응식
[CH:1](=[CH:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.F[B-](F)(F)F.O1CCCC1>CO>[C:2]1([CH:1]=[CH:8][CH:9]([OH:11])[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 159094-Phenyl-3-Buten-2-oneHCID 26255TetrafluoroborateHCID 634876Binap, (A+-)-

생성물 1

HCID 151724-Phenylbut-3-en-2-ol수율 34.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

In a 200 ml stainless steel autoclave were charged 5 g (34.2 mmole) of benzalacetone and 0.213 g (0.171 mmole) of ##STR24## ((+)-BINAP)}BF4 synthesized in Example 4, and 3 ml of tetrahydrofuran and 2 ml of methanol were added thereto, followed by allowing the mixture to react at 30° C. under a hydrogen pressure of 50 kg/cm2 for 45 hours. The solvent was removed by distillation under reduced pressure (10 mmHg), and the reaction product was analyzed by GLC (PEG HT, 25 m, produced by Gasukuro Kogyo K. K.) to find the conversion to be 34.5%. The product was separated into the unreacted ketone and the hydrogenation product by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 by volume) to obtain 1.73 g of 4-phenyl-3-buten-2-ol having a purity of 89%. {α}25 D : +18.1°(c=5, CS2).

후처리

  1. additionwere added
  2. customto react at 30° C. under a hydrogen pressure of 50 kg/cm2 for 45 hours
  3. customThe solvent was removed by distillation under reduced pressure (10 mmHg)
  4. customthe reaction product was analyzed by GLC (PEG HT, 25 m, produced by Gasukuro Kogyo K. K.)
  5. customThe product was separated into the unreacted ketone

출처 및 근거

ORD 기록
ord-ea4636c2ea984d078b6dc3a3f070d495
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159093

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