Acetic Acid → HCID 86702791, 화합물

HRID 718555

반응식

HRID 718555 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86702791HCID 86702791, 화합물수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c534bb7fff64b7e84363882a9867388
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193935B2

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