Acetic Acid → HCID 86702791、化合物

HRID 718555

反応式

HRID 718555 の反応式
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:10][C:5]=2[O:4][CH2:3]1.[C:31]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH:42]([CH3:45])[CH:43]=O)=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32].CC(O)=O>C1COCC1>[C:31]([C:35]1[CH:36]=[CH:37][C:38]([CH2:41][CH:42]([CH3:45])[CH:43]=[CH:11][C:9]2[CH:8]=[CH:7][C:6]3[O:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[CH:39][CH:40]=1)([CH3:34])([CH3:33])[CH3:32]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 228987LilialHCID 10695955(Benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide

生成物 1

HCID 86702791HCID 86702791、化合物収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

Potassium t-butylat (1 Min THF, 11 mL, 11.0 mmol, 1.1 equiv.) was added to a solution of (benzo[d][1,3]dioxol-5-ylmethyl)triphenylphosphonium bromide (4.77 g, 10.0 mmol, 1.0 equiv.) in THF (20 mL) at 25° C. After the dark red suspension was stirred at 25° C. for 10 min, 3-(4-tert-butylphenyl)-2-methylpropanal (2.04 g, 10.0 mmol, 1.0 equiv.) in THF (10 mL) was added, and the mixture was stirred at 70° C. for 1.5 h. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was extracted with hexanes, the combined organic phases were dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 19:1) to yield 2.83 g (88%) of the title compound as a yellow oil.

後処理

  1. stirringthe mixture was stirred at 70° C. for 1.5 h
  2. extractionthe aqueous layer was extracted with hexanes
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography on SiO2 (hexanes/EtOAc 19:1)

出典と根拠

ORDレコード
ord-7c534bb7fff64b7e84363882a9867388
出典データセット
uspto-grants-2015_11
特許番号
US09193935B2

関連ノート

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