Ethyl bromoacetate → Ethyl 4-[(7,8-dihydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate

HRID 1237

反応式

HRID 1237 の反応式
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C:9]1([CH3:33])[C:18]2[CH:17]=[C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=3)[CH:15]=[CH:14][C:13]=2[C:12](=[O:32])[CH2:11][CH2:10]1>C1C=CC=CC=1.[Zn]>[OH:32][C:12]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:11][CH2:10][C:9]([CH3:8])([CH3:33])[C:18]2[CH:17]=[C:16]([C:19]#[C:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:30][CH:31]=3)[CH:15]=[CH:14][C:13]1=2

参加物

5

反応物 2

HCID 7748Ethyl bromoacetateHCID 15345545Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate2 回

生成物 1

HCID 18314576Ethyl 4-[(7,8-dihydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoate

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 241Benzene溶媒

実験手順

To a refluxing solution of 1.00 g (15.30 mmol) of 20 mesh, granular zinc (activated prior to use by washing with 2% HCl, water, 95% ethanol, acetone, anhydrous Et2O and then dried in vacuum for several hours) in 20 ml of dry benzene was slowly added a mixture of 0.23 ml (1.62 mmol) of ethyl bromoacetate, 0.28 g (0.81 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate (Compound 1) in 10 ml of dry benzene. The resulting mixture was refluxed for 2 hours, cooled to room temperature and the precipitate filtered through celite. The filtrate was washed with cold 15% H2SO4, sat. aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo to a yellow oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a light yellow solid.

後処理

  1. washby washing with 2% HCl, water, 95% ethanol, acetone, anhydrous Et2O
  2. dry with materialdried in vacuum for several hours) in 20 ml of dry benzene
  3. additionwas slowly added
  4. temperatureThe resulting mixture was refluxed for 2 hours
  5. filtrationthe precipitate filtered through celite
  6. washThe filtrate was washed with cold 15% H2SO4, sat. aqueous NaHCO3 and brine
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated in vacuo to a yellow oil
  9. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-3bc3da49cb6b461196d4eaac084da60d
出典データセット
uspto-grants-1998_03
特許番号
US05723620

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