Pivalic acid → 8-chloro-2,3,4,6-tetrahydro-1H-dibenzo[c,h]chromen-1-one

HRID 1412932

反応式

HRID 1412932 の反応式
C(O)(=O)C(C)(C)C.C(=O)([O-])[O-].[K+].[K+].Br[C:15]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:16]=1[CH2:17][O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][CH2:23][C:24]2=[O:29]>CC(N(C)C)=O.C([O-])(=O)C(C)(C)C.[Pd+2].C([O-])(=O)C(C)(C)C.FC1C=CC(P(C2C=CC(F)=CC=2)C2C=CC(F)=CC=2)=CC=1>[Cl:34][C:31]1[CH:32]=[CH:33][C:15]2[C:28]3[C:19](=[C:20]4[CH2:21][CH2:22][CH2:23][C:24](=[O:29])[C:25]4=[CH:26][CH:27]=3)[O:18][CH2:17][C:16]=2[CH:30]=1

参加物

7

反応物 3

HCID 6417Pivalic acidHCID 11430Potassium CarbonateHCID 696731795-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one

生成物 1

HCID 866883328-chloro-2,3,4,6-tetrahydro-1H-dibenzo[c,h]chromen-1-one収率 97.4%

試薬・触媒・溶媒 3

HCID 140387Tris(4-fluorophenyl)phosphine触媒HCID 24905427palladium(II) pivalate触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
60 °C

実験手順

To a flask containing palladium(II) pivalate (68 mg, 0.22 mmol), tri(4-fluorophenyl)phosphine (70 mg, 0.22 mmol), pivalic acid (135 mg, 1.3 mmol) and potassium carbonate (1.83 g, 13.1 mmol) was added a solution of 5-(2-bromo-5-chlorobenzyloxy)-3,4-dihydronaphthalen-1(2H)-one (1.61 g, 4.4 mmol) in dimethyacetamide (23 mL). The flask was evacuated and backfilled with argon 5 times and then stirred under argon at 60° C. for 24 hours. The reaction was poured directly onto a silica gel column and purified by flash column chromatography (hexanes/DCM) to yield 8-chloro-2,3,4,6-tetrahydro-1H-dibenzo[c,h]chromen-1-one (1.22 g, 97% yield) as an off-white solid.

後処理

  1. customThe flask was evacuated
  2. additionThe reaction was poured directly onto a silica gel column
  3. custompurified by flash column chromatography (hexanes/DCM)

出典と根拠

ORDレコード
ord-319a701b29b24c5580fdef94cf8c6809
出典データセット
uspto-grants-2014_12
特許番号
US08921341B2

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