HCID 11658454, 화합물 → HCID 11658461, 화합물

HRID 13721노트

반응식

HRID 13721 반응식
C(C=C=O)CCC.[CH2:8]([C@H:12]1[C:13](=[O:21])[O:14]/[C:15]/1=[CH:16]\[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH2:10][CH3:11]>ClCCl>[CH2:8]([C@@H:12]1[C@H:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[O:14][C:13]1=[O:21])[CH2:9][CH2:10][CH3:11]

참가 물질

4

반응물 2

HCID 11658454HCID 11658454, 화합물HCID 130548641-Hexen-1-one

생성물 1

HCID 11658461HCID 11658461, 화합물수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The purified n-butyl ketene dimer 2a, (5.1 mmol, 1.0 g) was dissolved in 40 mL dichloromethane (0.1 M) and transferred to a Parr bomb apparatus under a N.sub.2 atmosphere using an additional 10 mL dichloromethane as wash solvent. Pd/C (107 mg, 1 mol %, 5 wt %) was then added at one time under N.sub.2 atmosphere. The Parr bomb was then subjected to three consecutive evacuation-saturation cycles of hydrogen gas and then pressurized to 30 psi hydrogen gas pressure. Hydrogenation with shaking (Parr shaker) was continued for 30 min at this pressure and then the heterogeneous slurry was vacuum filtered through a plug of Celite, and concentrated yielding a colorless oil. Flash chromatography with gradient elution (5→15% diethyl ether/hexanes; 2.5×35.0×5 cm pad) gave 3-butyl-4-pentyl-oxetan-2-one (3a, 897 mg, 90%) as a colorless oil (>96% ee, chiral GC): Rf 0.47 (15% Et2O:hexanes ); IR (thin film) 1824 cm−1; 1H NMR (300 MHz, CDCl.sub.3) δ 4.54 (ddd, J=2.1, 3.6, 5.7 Hz, 1H), 3.59 (ddd, J=4.5, 5.4, 8.4 Hz, 1H), 1.46-1.84(m,6H), 1.31-1.44 (m, 8H), 0.88-0.94 (m, 6H); 13C NMR (500 MHz, CDCl3) δ 173.1, 76.5, 53.3, 32.2, 30.9, 30.5, 26.0, 24.4, 23.2, 23.2, 14.7, 14.5; ESI LRMS Calcd. for C12H22O2 [M+Li]: 205: Found:205.

후처리

  1. washas wash solvent
  2. additionPd/C (107 mg, 1 mol %, 5 wt %) was then added at one time under N.sub
  3. filtrationfiltered through a plug of Celite
  4. concentrationconcentrated
  5. customyielding a colorless oil
  6. washFlash chromatography with gradient elution (5→15% diethyl ether/hexanes; 2.5×35.0×5 cm pad)

출처 및 근거

ORD 기록
ord-7d4250798a884f5787bd97168c8b54bd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728153B2

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