Propylene Oxide → HCID 89463680, compound

HRID 881973Notes

Reaction equation

HRID 881973 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:14]1[O:17][CH:15]1C.[C:18]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:17][C@H:15]([CH3:14])[CH2:13][O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][CH3:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 11430Potassium CarbonateHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 89463680HCID 89463680, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound methyl 3-hydroxy-5-methoxybenzoate (Example 1, step i, 90 mg, 0.5 mmol) and propylene oxide (120 mg, 2 mmol) in DMF (2 ml) was added K2CO3 (280 mg, 2 mmol). The reaction mixture was stirred at 100° C. overnight. After cooling to ambient temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified using normal phase chromatography, eluting with petroleum ether containing 50% ethyl acetate to give (R)-methyl 3-(2-hydroxypropoxy)-5-methoxybenzoate (100 mg).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified
  5. washeluting with petroleum ether containing 50% ethyl acetate

Sources & evidence

ORD record
ord-9f11c1f347c444ff998c840dcb238ea8
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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