Ethanol → HCID 66839108, compound

HRID 546704Notes

Reaction equation

HRID 546704 reaction equation
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][CH:7]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:8]([O:10]CC)=[O:9].C(O)C.O>C1COCC1.C(OCC)C>[Cl:3][CH2:4][CH2:5][CH2:6][CH:7]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 66839381HCID 66839381, compound

Product 1

HCID 66839108HCID 66839108, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 5 N sodium hydroxide solution (1.6 ml) was added to a solution of ethyl 5-chloro-2-(tetrahydropyran-4-yl)-valerate (672 mg) in THF (2.5 ml)-ethanol (7.5 ml), and the reaction solution was stirred at room temperature for four days. Water and diethyl ether were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was washed with diethyl ether again. Then, 5 N hydrochloric acid (1.6 ml) and ethyl acetate were added to the aqueous layer, and the organic layer was separated. The ethyl acetate extraction layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain crude 5-chloro-2-(tetrahydropyran-4-yl)valeric acid (442 mg).

Workup

  1. customthe aqueous layer was separated
  2. washThe aqueous layer was washed with diethyl ether again
  3. additionThen, 5 N hydrochloric acid (1.6 ml) and ethyl acetate were added to the aqueous layer
  4. customthe organic layer was separated
  5. extractionThe ethyl acetate extraction layer
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2dc16bb6f1ab45c59033c2b6c70236a9
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…