Tetrahydrofuran → tert-Butyl cyclopentylacetate

HRID 1475630Notes

Reaction equation

HRID 1475630 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].C1COCC1.[CH:12]1([CH2:17][C:18](Cl)=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl-].[NH4+]>>[CH:12]1([CH2:17][C:18]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 3485182Cyclopentylacetyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 10797592tert-Butyl cyclopentylacetate

Procedure

136 ml of a 1 M solution of potassium tert-butoxide in THF (136 mmol) were cooled to 0° C., and 21.0 g (143.2 mmol) of cyclopentylacetic chloride were added dropwise. After the addition had ended, the suspension was warmed to RT and stirred overnight and then added to saturated aqueous ammonium chloride solution. The mixture was extracted three times with diethyl ether. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The desired product was isolated from the residue by kugelrohr distillation (1.6 mbar/160-180° C.). This gave 17.58 g of the target compound (66.6% of theory).

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted three times with diethyl ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71af504e5f32468490c7a90652ed2b86
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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