Acetone → HCID 86668126、化合物

HRID 2171736ノート

反応式

HRID 2171736 の反応式
[CH2:1]([C@@H:3]1O[CH2:4]1)Cl.C[C:7]1(C)[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH3:24]C(C)=O>>[CH3:1][C:3]([O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[CH2:7][CH2:8][CH2:9]2)([C@@H:4]1[CH2:18][O:21]1)[CH3:24]

参加物

5

反応物 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 2734062(-)-EpichlorohydrinHCID 23014065HCID 23014065、化合物

生成物 1

HCID 86668126HCID 86668126、化合物収率 67%

反応条件

温度
45 °C

実験手順

To a mixture of (R)-epichlorohydrin (0.93 g, 10 mmol) and 1,1-dimethyl-indan-5-ol (0.81 g, 5.0 mmol) in acetone (30 ml) was added potassium carbonate (0.69 g, 5 mmol). The mixture was stirred at 45° C. for 96 hours. The reaction mixture was then concentrated. The residue was partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic phases were combined and washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by flash chromatography (silica, methylene chloride/heptane) to give 9.18 g (67%) of (S)-2-(1,1-dimethyl-indan-5-yloxymethyl)-oxirane.

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionextracted twice with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by flash chromatography (silica, methylene chloride/heptane)

出典と根拠

ORDレコード
ord-71c43c6174ef4ff3a5beb5eee1d6b4e8
出典データセット
uspto-grants-2015_06
特許番号
US09051331B2

反応ノート

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