Methanol → Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

HRID 1894306Notes

Reaction equation

HRID 1894306 reaction equation
CCN([CH:7]([CH3:9])C)C(C)C.Cl[C:11]([O:13][CH2:14][CH3:15])=O.[BH4-].[Na+].C[OH:19].C1[CH2:24][O:23]CC1>CCOC(C)=O.O>[OH:23][CH2:24][C:15]1([C:14]([O:13][CH3:11])=[O:19])[CH2:9][CH2:7]1

Participants

8

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydride

Product 1

HCID 22934721Methyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The above product was mixed with DIPEA (1.2 eq) in THF and stirred at 0° C. for 10 minutes, to the reaction was added ethyl chloroformate (1 eq) slowly and further stirred for 1.5 hours from 0° C. to RT. To the reaction cooled at 0° C. was added NaBH4 (1.5 eq) slowly followed by MeOH (2 eq) and stirred for 2 hours from 0° C. to RT. The reaction was diluted with EtOAc, water and extracted with EtOAc three times. The combined organic layer was washed with water, brine and dried. The solution was evaporated and purified with silica gel column to give methyl 1-(hydroxymethyl)cyclopropanecarboxylate (2.5 g).

Workup

  1. stirringfurther stirred for 1.5 hours from 0° C. to RT
  2. temperatureTo the reaction cooled at 0° C.
  3. stirringstirred for 2 hours from 0° C. to RT
  4. extractionextracted with EtOAc three times
  5. washThe combined organic layer was washed with water, brine
  6. customdried
  7. customThe solution was evaporated
  8. custompurified with silica gel column

Sources & evidence

ORD record
ord-fd6c27a89963476b8f3cc7b9d16363e9
Source dataset
uspto-grants-2013_08
Patent number
US08513283B2

Reaction notes

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