Trifluoroacetate → 3'H-Spiro[cyclohexane-1,1'-isobenzofuran]-4-one

HRID 432596ノート

反応式

HRID 432596 の反応式
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:19])[CH2:18][CH2:17][C:12]2([O:16]CCO2)[CH2:11][CH2:10]1.FC(F)(F)C([O-])=O>CCCCCC.CCOCC>[C:9]12([CH2:10][CH2:11][C:12](=[O:16])[CH2:17][CH2:18]1)[C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][O:19]2

参加物

4

反応物 2

HCID 84468TrifluoroacetateHCID 187600538-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

生成物 1

HCID 187601133'H-Spiro[cyclohexane-1,1'-isobenzofuran]-4-one収率 44%

試薬・触媒・溶媒 1

HCID 21584099Diethylether hexane溶媒

実験手順

0.64 g (2.62 mmol) of 8-(2-Hydroxymethyl-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol was added to 80% trifluoroacetate (TFA) 2.5 ml. The mixture was stirred at room temperature for 5 hours. Rotory evaporation of the TFA left thick brown oil. The oil was dissolved in 2.0 ml of EtOAc and washed first with 1N NaOH and then with H2O. The organic layer was dried with MgSO4 and concentrated, leaving a thick yellow oil. Hexane/ether (2:1) was added and the sides of the flask were scratched. A precipitate began to form. 0.23 Grams of 3′H-Spiro[cyclohexane-1,1′-isobenzofuran]-4-one were obtained, 44% yield.

後処理

  1. customRotory evaporation of the TFA
  2. waitleft thick brown oil
  3. dissolutionThe oil was dissolved in 2.0 ml of EtOAc
  4. washwashed first with 1N NaOH
  5. dry with materialThe organic layer was dried with MgSO4
  6. concentrationconcentrated
  7. customleaving a thick yellow oil
  8. customto form

出典と根拠

ORDレコード
ord-f1168dc3b88040e0bdff1ff2f0caefdd
出典データセット
uspto-grants-2003_12
特許番号
US06664258B1

反応ノート

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