Ethyl bromoacetate → 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene

HRID 380109ノート

反応式

HRID 380109 の反応式
ClCCl.B(Br)(Br)Br.[CH3:8][N:9]([CH:28]1[C:36]2[C:31](=[C:32]([OH:37])[CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:10][C:11]1[O:12][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C([O-])([O-])=O.[K+].[K+]>ClCCl.CN(C=O)C>[CH3:8][N:9]([CH:28]1[C:36]2[C:31](=[C:32]([O:37][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:10][C:11]1[O:12][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:15]=1

参加物

7

反応物 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 183672371-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indeneHCID 22277759Boron tribromide dichloromethane

生成物 1

HCID 183673111-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene収率 60.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-[N-methyl-N-[(4,5-diphenyloxazol-2.-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (109 mg) in dichloromethane (2 ml) was added 1M boron tribromide dichloromethane solution (1 ml) at 0° C. After being stirred for 4 hours at 0° C., the solvent was evaporated in vacuo. The residue was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo to afford crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg). To a solution of crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg) and ethyl bromoacetate (80 mg) in DMF (3 ml) was added K2CO3 (80 mg). After being stirred for 24 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-ethoxycarbonylmethoxy-1H-indene (80 mg).

後処理

  1. customthe solvent was evaporated in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe mixture was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto afford crude 1-[N-methyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-hydroxy-1H-indene (109 mg)
  7. stirringAfter being stirred for 24 hours
  8. extractionthe solution was extracted with ethyl acetate
  9. washThe mixture was washed with brine
  10. dry with materialdried over MgSO4
  11. customevaporated in vacuo
  12. customThe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-7c73874897b84d00a0f8b693aa129af1
出典データセット
uspto-grants-2001_10
特許番号
US06300344B1

反応ノート

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