(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 1195480ノート

反応式

HRID 1195480 の反応式
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

参加物

4

反応物 1

HCID 86745750(Z)-5-(2,5-dihydroxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl acetate

生成物 1

HCID 22843764(S)-3,4-dihydro-2,5,7,8-tetramethyl-2-vinyl-2H-[1]-benzopyran-6-ol収率 86.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-331d439b3ade4588b4a4e5069a25e3c4
出典データセット
uspto-grants-1992_05
特許番号
US05110955

反応ノート

読み込み中…