Pyridine → 16-Hexadecanoyloxyhexadecanoic acid

HRID 1603972노트

반응식

HRID 1603972 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].N1C=CC=CC=1.[C:26](Cl)(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>O1CCCC1>[C:26]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:42])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 8206Palmitoyl chlorideHCID 1046616-Hydroxyhexadecanoic acid

생성물 1

HCID 1960674616-Hexadecanoyloxyhexadecanoic acid수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

16-Hydroxyhexadecanoic acid (5.43 g, 19.9 mmol) was dissolved in tetrahydrofuran (190 ml) and pyridine (2.36 g, 29.9 mmol) was added. Palmitoyl chloride (5.48 g, 19.9 mmol) was dissolved in tetrahydrofuran (10 ml) and added dropwise at room temperature. After stirring at room temperature for 16 hours, the mixture was filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in chloroform, washed with water (3×50 ml), and the organic phase was dried (MgSO4). After evaporating under reduced pressure, the residue was purified on a silica column, eluting with chloroform with increasing methanol concentration (from 1% to 2% methanol in chloroform) to give 8.41 g (83%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 0.85 (t, 3H, CH3), 1.20-1.35 (s, 46H, --CH2 --), 1.55-1.70 (m, 6H, --CH2 --), 2.25 (t, 2H, --CH2 --C(O)--O), 2.45 (t, 2H, --CH2 --COOH), 4.05 (t, 2H, --O--CH2). 13C NMR (75 MHz, CDCl3): δ 14.01, 22.57, 24.10, 24.91, 25.82, 28.53, 28.75, 28.94, 29.08, 29.15, 29.25, 29.36, 29.54, 31.81, 34.29, 35.16, 64.27, 76.48, 76.90, 77.10, 77.32, 169.50, 173.91.

후처리

  1. additionadded dropwise at room temperature
  2. filtrationthe mixture was filtered
  3. customthe filtrate evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water (3×50 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customAfter evaporating under reduced pressure
  8. customthe residue was purified on a silica column
  9. washeluting with chloroform with increasing methanol concentration (from 1% to 2% methanol in chloroform)

출처 및 근거

ORD 기록
ord-529f7f01d19b441bacd19d9b17fabfdc
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990263

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