Acetone → HCID 86668126, 화합물

HRID 2171736노트

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HRID 2171736 반응식
[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]

참가 물질

5

반응물 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 2734062(-)-EpichlorohydrinHCID 23014065HCID 23014065, 화합물

생성물 1

HCID 86668126HCID 86668126, 화합물수율 67%

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온도
45 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-71c43c6174ef4ff3a5beb5eee1d6b4e8
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051331B2

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