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

HRID 1195482ノート

反応式

HRID 1195482 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.[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

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 3033859Calcium hydrideHCID 19819049(E)-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 67%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-c164f9981cbf4bf89597af5800d473d6
出典データセット
uspto-grants-1992_05
特許番号
US05110955

反応ノート

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