Acetone → HCID 86668126, compound

HRID 2171736Notes

Reaction equation

HRID 2171736 reaction equation
[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]

Participants

5

Reactant 4

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

Product 1

HCID 86668126HCID 86668126, compoundYield 67%

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-71c43c6174ef4ff3a5beb5eee1d6b4e8
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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