(Z)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate → (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol

HRID 1195480노트

반응식

HRID 1195480 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>CS(C)=O.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

4

반응물 1

HCID 86745750(Z)-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 86.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

A solution of 125 mg (0.43 mmol) of (Z)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate, 8 mg (3%) of (S)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthalene and 2.3 mg (1.5%) of π-allylpalladium chloride dimer in DMSO (3 ml) was left at 60° C. for 17 hours. After cooling the mixture was diluted with water and extracted with ether. The extracts were washed with water, dried, concentrated and the residue was purified as in Experiment 1, yielding 86 mg of (S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol. O.P. 36%.

후처리

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ether
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified as in Experiment 1

출처 및 근거

ORD 기록
ord-331d439b3ade4588b4a4e5069a25e3c4
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110955

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