Acetoacetic Acid → 10-(Cholest-5-en-3beta-oxy)decanal

HRID 1471359노트

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HRID 1471359 반응식
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CC(CC(O)=O)=O>ClCCl>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=[O:39])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

참가 물질

4

반응물 2

HCID 96Acetoacetic AcidHCID 86665351HCID 86665351, 화합물

생성물 1

HCID 8666535010-(Cholest-5-en-3beta-oxy)decanal

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 100 mL round-bottomed flask was solid supported 2,2,6,6-Tetramethyl Piperidinyloxy, Free Radical (0.5 g, 1.1 mmol/g, 0.553 mmol) and 10-(Cholest-5-en-3β-oxy)decan-1-ol (3.00 g, 5.53 mmol) suspended in dichloromethane (20 ml) to give a colorless suspension. lodobenzene diacetate (1.958 g, 6.08 mmol) was added to the mixture, which was allowed to stir overnight at room temperature. The reaction mixture was filtered and the solid support washed with DCM. The combined filtrate was washed with saturated sodium thiosulfate (2×20 mL) and brine (1×20 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The resultant oil was purified via column chromatography with 100% DCM as mobile phase to give 2.70 g (90%) of a colorless wax. 1H NMR (300 MHz, CDCl3) δ0.69 (3H, s); 0.84-1.74 (47H, m); 1.76-2.09 (5H, m); 2.12-2.26 (1H, m); 2.32-2.40 (1H, m); 2.44 (2H, dt, J=7.4, 1.9 Hz); 3.14 (1H, tt, J=11.2, 4.4 Hz); 3.46 (2H, t, J=6.9 Hz); 5.35 (1H, d, J=5.3 Hz); 9.78 (1H, t, J=1.9 Hz).

후처리

  1. customIn a 100 mL round-bottomed flask was
  2. customto give a colorless suspension
  3. filtrationThe reaction mixture was filtered
  4. washthe solid support washed with DCM
  5. washThe combined filtrate was washed with saturated sodium thiosulfate (2×20 mL) and brine (1×20 mL)
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resultant oil was purified via column chromatography with 100% DCM as mobile phase
  10. customto give 2.70 g (90%) of a colorless wax

출처 및 근거

ORD 기록
ord-e7a16d2f03174a678bab69dd6fd0fd67
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012225B2

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