Water → HCID 86665239, 화합물

HRID 1028086노트

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HRID 1028086 반응식
[OH-].[Na+].[CH2:3]([OH:21])[CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20].[C:22]([O:26][C:27](=[O:32])[CH:28](Br)[CH2:29][CH3:30])([CH3:25])([CH3:24])[CH3:23].O>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCCC>[CH2:3]([O:21][CH:28]([CH2:29][CH3:30])[C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:32])[CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

참가 물질

8

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13124118tert-Butyl 2-bromobutanoate2회HCID 86665240HCID 86665240, 화합물

생성물 1

HCID 86665239HCID 86665239, 화합물수율 60.4%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매HCID 8900Heptane용매

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온도
50 °C

실험 절차

An aqueous solution of sodium hydroxide (50% (w/w), 6 mL) was added portionwise to a mixture of (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaen-1-ol (1.66 g, 6.37 mmol), tert-butyl-2-bromobutyrat (2.86 g, 12.8 mmol) and tetrabutylammonium bisulfate (0.65 g, 1.91 mmol) in toluene (12 ml). The reaction mixture was vigorously stirred under N2-atmosphere and warmed to 50° C. The reaction mixture was stirred at 50° C. for a total of 25 hrs. Additional tert-butyl-2-bromobutyrat (1.43 g, 6.41 mmol) and (1.42 g, 6.38 mmol) was added after 1½ hrs and 3 hrs respectively. The mixture was cooled to room temperature and added water (30 mL) and heptane (50 mL), the resulting two phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated under reduced pressure. Flash chromatography on silica gel (30 g) eluting with heptane-heptane/EtOAc (99:1) yielded 1.55 g of the title compound as a liquid. 1H NMR (300 MHz, CDCl3) δ 0.96 (t, 3H), 0.97 (t, 3H), 1.48 (s, 9H), 1.64-1.86 (m, 2H), 2.03-2.12 (m, 2H), 2.39 (dd, J=12.1, 6.7 Hz, 2H), 2.79-2.86 (m, 8H), 3.29-3.37 (m, 1H), 3.57-3.66 (m, 2H), 5.27-5.49 (m, 10H).

후처리

  1. stirringThe reaction mixture was stirred at 50° C. for a total of 25 hrs
  2. temperatureThe mixture was cooled to room temperature
  3. customthe resulting two phases were separated
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. washFlash chromatography on silica gel (30 g) eluting with heptane-heptane/EtOAc (99:1)

출처 및 근거

ORD 기록
ord-dc0563c60dea463bbaf7cdb41592ef5f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735436B2

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