Water → 4-Isobutyl-dihydro-furan-2-one

HRID 458070노트

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HRID 458070 반응식
[H-].[Na+].C([O:7][C:8](=[O:18])[CH2:9][CH:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](O)=O)(C)(C)C.O>C1COCC1>[CH2:14]([CH:10]1[CH2:11][O:18][C:8](=[O:7])[CH2:9]1)[CH:15]([CH3:16])[CH3:17]

참가 물질

5

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 99427122-Isobutyl-succinic acid-4-t-butyl ester

생성물 1

HCID 152136444-Isobutyl-dihydro-furan-2-one수율 104.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Triethyl phosphonoacetate (1.13 mL, 5.70 mmol) was added dropwise to a stirring suspension of sodium hydride (0.22 g of a 60% dispersion in oil, 5.43 mmol) in THF (15 mL) at 0° C. under argon. After 20 minutes, ketone 3 (0.75 g, 5.43 mmol) in THF (6 mL) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 16 hours. Water (5 mL) was added, and the mixture was extracted with ether (15 mL×3). The combined organic fractions were washed with brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5) to give the ester 4 (0.81 g, 72%) as a colorless oil; Rf(heptane/ethyl acetate, 8:2) 0.66; νmax(film)/cm−1 1715 (C═O), 1652 (C═C); δH (400 MHz; CDCl3): 5.80 (1H, quint, J=2.2, CHCO2Et), 4.15 (2H, q, J=7.1, CO2CH2Me), 2.79 (1H, dd, J=19.5, 8.1), 2.69 (1H, ddt, J=19.8, 7.3, 2.3), 2.47 (1H, dd, J=17.3, 7.2), 2.34 (1H, ddt, J=17.3, 5.6, 1.8), 2.14 (1H, m), 2.02 (1H, m), 1.60–1.22 (8H, m); m/z (ES+) 209 (M+H, 57%), 455 (2M+K, 67).

후처리

  1. extractionthe mixture was extracted with ether (15 mL×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5)

출처 및 근거

ORD 기록
ord-90e800f79c6749d780c5b56ab4394afa
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189747B2

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