Water → Distearyl Ether

HRID 2375757

반응식

HRID 2375757 반응식
[H-].[Na+].C[C:4]1([CH3:11])O[C@H:7]([CH2:9]O)[CH2:6][O:5]1.C(Br)C[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].O>C1COCC1>[CH2:6]([O:5][CH2:4][CH2:11][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])[CH2:7][CH2:9][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 82181-BromooctadecaneHCID 24758Sodium hydrideHCID 736056(R)-Solketal

생성물 1

HCID 80526Distearyl Ether수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
80 °C

실험 절차

To a stirred suspension of NaH (80%; 0.55 g, 17.4 mmol, 2 equiv) in THF (20 ml) was added dropwise a solution of (R)-glycerol acetonide 1 (1.15 g; 1 equiv) in THF (20 ml). After that octadecyl bromide (5.8 g, 17.4 mmol, 2 equiv) dissolved in THF (25 ml) was added dropwise and the mixture obtained was stirred overnight at 80° C. The reaction mixture was cooled to 0° C. and water was added. The resulting mixture was concentrated and the residue was extracted with water and diethyl ether and the combined extracts were dried (MgSO4). The crude product obtained was further purified by flash column chromatography (10% ethyl acetate-n-hexane) to yield the title compound 1b (2.03 g, 5.28 mmol, 61%).

후처리

  1. additionwas added dropwise
  2. customthe mixture obtained
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. concentrationThe resulting mixture was concentrated
  5. extractionthe residue was extracted with water and diethyl ether
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. customThe crude product obtained
  8. customwas further purified by flash column chromatography (10% ethyl acetate-n-hexane)

출처 및 근거

ORD 기록
ord-5c0e6097f7454a8ebf3a75ff760da7a9
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465817B2

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