Hydrochloric Acid → Diethyl 2-(3-(2,6-dimethylbenzyloxy)benzoyl)pentanedioate

HRID 73446

反応式

HRID 73446 の反応式
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=1.CC(C)([O-])C.[K+].Br[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].Cl>C(O)(C)(C)C>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:12]([CH:13]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 68320Ethyl 3-bromopropionateHCID 23665647Potassium tert-butoxideHCID 66875194Ethyl 3-(3-(2,6-dimethylbenzyloxy)phenyl)-3-oxopropanoate

生成物 1

HCID 66875332Diethyl 2-(3-(2,6-dimethylbenzyloxy)benzoyl)pentanedioate

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of Ethyl 3-(3-(2,6-dimethylbenzyloxy)phenyl)-3-oxopropanoate (Step A, 5 g, 16.02 mmol) in t-butyl alcohol (50 ml) was added a solution of potassium tert-butoxide (1M in t-butyl alcohol, 1.988 g, 17.7 mmol) and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl 3-bromopropionate was added drop wise to the reaction mixture and stirring continued for another 2 hours and then poured into 1M HCl, extracted with ethyl acetate (2×), washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography eluted with hexane:ethyl acetate (2:1) to give the title compound.

後処理

  1. stirringstirring
  2. waitcontinued for another 2 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography
  9. washeluted with hexane:ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-8731ede7ec354442beb9aed4ad52a959
出典データセット
uspto-grants-2014_09
特許番号
US08829058B2

関連ノート

読み込み中…