Potassium Carbonate → Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

HRID 1849521ノート

反応式

HRID 1849521 の反応式
[CH3:1][C:2]1([CH3:13])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[O:3]1.Br[CH2:15][C:16]1[C:28]([Cl:29])=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:18]([F:30])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:29][C:28]1[C:16]([CH2:15][O:12][C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][CH2:11][C:2]([CH3:13])([CH3:1])[O:3]3)=[CH:8][CH:7]=2)=[CH:17][C:18]([F:30])=[C:19]([CH:27]=1)[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-olHCID 86702928HCID 86702928、化合物

生成物 1

HCID 86702867Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2,2-dimethylchroman-7-ol (100 mg, 0.561 mmol), tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (191 mg, 0.590 mmol) and potassium carbonate (194 mg, 1.40 mmol) in acetone (30 mL) was stirred at 50° C. for 16 hrs. After cooling to room temperature, the mixture was extracted with EtOAc (150×5 mL). The combined orgaic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was used in next step without further purification (290 mg, crude). LCMS (ESI) m/z: 420.8 [M+H].

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc (150×5 mL)
  3. washThe combined orgaic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-931b74e83ade41afb5978745ec36b14b
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

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