Potassium Carbonate → HCID 13755497, compound

HRID 979891Notes

Reaction equation

HRID 979891 reaction equation
[O:1]1[CH2:12][C@H:2]1[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:13]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCCCCC>[CH2:5]([O:4][CH2:3][C@H:2]([OH:1])[CH2:12][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][CH2:16][CH:13]1[CH2:14][CH2:15]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 146296Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI)HCID 13755494HCID 13755494, compound

Product 1

HCID 13755497HCID 13755497, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

A mixture of (S)-benzyl 2,3-epoxypropyl ether (8.95 g as described in Heterocycles Vol. 16, 381, 1981), o-cyclopropylmethoxyphenol (8.95 g) in 36 ml acetone and 4 ml hexane, to which is added powdered potassium carbonate (6.9 g), is stirred at reflux in nitrogen atmosphere for 74 hours. After cooling to room temperature the solid is filtered off and washed with acetone. The filtrate is concentrated under reduced pressure, the residue is dissolved in ether, the ether solution is washed 2x with water and dried over anhydrous sodium sulfate, filtered, and the filtrate is evaporated to dryness. The crude oil is distilled in vacuo, at 199°-212°/0.2 mm to yield (S)-1-benzyloxy-3-[o-(cyclopropylmethoxy)phenoxy]-2-hydroxypropane.

Workup

  1. temperatureat reflux in nitrogen atmosphere for 74 hours
  2. filtrationis filtered off
  3. washwashed with acetone
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. dissolutionthe residue is dissolved in ether
  6. washthe ether solution is washed 2x with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated to dryness
  10. distillationThe crude oil is distilled in vacuo, at 199°-212°/0.2 mm

Sources & evidence

ORD record
ord-92c9089d9db24ee3b1e9ad23dfc14eb9
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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