Water → (1R,2R)-1,2-Cyclopentanedimethanol

HRID 1441082Notes

Reaction equation

HRID 1441082 reaction equation
[C@@H:1]1([C:8](Cl)=[O:9])[CH2:4][CH2:3][C@H:2]1[C:5](Cl)=[O:6].[BH4-].[Na+].O.[Cl-].[Na+].O1CCC[CH2:17]1>C(O)C.C(OCC)C>[OH:9][CH2:8][C@@H:1]1[CH2:4][CH2:3][CH2:17][C@H:2]1[CH2:5][OH:6]

Participants

8

Reactant 5

HCID 962Water2×HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 144612573668-43-7

Product 1

HCID 11286477(1R,2R)-1,2-Cyclopentanedimethanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

A solution of 20 g of trans-1,2-cyclobutanedicarboxylic acid dichloride in 40 ml of tetrahydrofuran is carefully instilled at -15° C. in a solution of 8.4 g of sodium borohydride in 280 ml of ethyl alcohol. After completion of the gas generation it is stirred for 30 minutes at -15° C. and then 150 ml of water is slowly instilled. It is stirred for 30 minutes at 22° C. and then diluted with 1.5 liter of diethyl ether. It is shaken twice with water, twice with semiconcentrated sodium chloride solution, dried on anhydrous sodium sulfate and concentrated by evaporation in a vacuum. The residue is purified by chromatography on silica gel. With ethyl acetate, 9.5 g of trans-1,2-dihydroxymethylcyclopentane is obtained as colorless liquid.

Workup

  1. stirringIt is stirred for 30 minutes at 22° C.
  2. dry with materialdried on anhydrous sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-accb6c79252f47969d5d2388792808ce
Source dataset
uspto-grants-1996_03
Patent number
US05502075

Reaction notes

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