Water → Distearyl Ether

HRID 2375757

反応式

HRID 2375757 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 80526Distearyl Ether収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
80 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5c0e6097f7454a8ebf3a75ff760da7a9
出典データセット
uspto-grants-2008_12
特許番号
US07465817B2

関連ノート

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