Ammonium Chloride → (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol

HRID 1195482노트

반응식

HRID 1195482 반응식
C(O[CH2:5]/[CH:6]=[C:7](\[CH3:21])/[CH2:8][CH2:9][C:10]1[C:15]([CH3:16])=[C:14]([OH:17])[C:13]([CH3:18])=[C:12]([CH3:19])[C:11]=1[OH:20])(=O)C.[H-].[Ca+2].[H-].[Cl-].[NH4+]>CS(C)=O>[CH3:21][C@@:7]1([CH:6]=[CH2:5])[CH2:8][CH2:9][C:10]2[C:15]([CH3:16])=[C:14]([OH:17])[C:13]([CH3:18])=[C:12]([CH3:19])[C:11]=2[O:20]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 3033859Calcium hydrideHCID 19819049(E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

생성물 1

HCID 22843764(S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol수율 67%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 106 mg (0.36 mmol) of (E)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate and 9 mg (3%) of [[(R)-6,6'-dimethyl-1,1'-biphenyl-2,2'-bis(diphenylphosphine)]-P,P'][(η-3)-2-propenyl]palladium perchlorate in 2 ml of DMSO was treated with 15 mg of calcium hydride and stirred at room temperature for three days. Thereafter, the mixture was poured into saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with water and dried. The residue remaining after removal of the solvent was purified as described in Experiment 1, yielding 56 mg of (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol. O.P. 33%.

후처리

  1. extractionextracted with ether
  2. washThe combined extracts were washed with water
  3. customdried
  4. customafter removal of the solvent
  5. customwas purified

출처 및 근거

ORD 기록
ord-c164f9981cbf4bf89597af5800d473d6
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110955

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