Water → HCID 13708900, compound

HRID 257709Notes

Reaction equation

HRID 257709 reaction equation
CCOCC.[F:6][C:7]([F:23])([F:22])[CH:8]([O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH2:9][C:10](OCC)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:23][C:7]([F:6])([F:22])[CH:8]([O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH2:9][CH2:10][OH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether2×HCID 13708886HCID 13708886, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13708900HCID 13708900, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Fifty milliliters of an ether solution of 30.1 g of ethyl 4,4,4-trifluoro-3-tetrahydropyranyloxybutyrate (1) were added dropwise to an ether suspension of 4.2 g of lithium aluminum hydride over a period of 1.5 hours. The mixture was further refluxed for 30 minutes, and a mixed solution of 8 g of water and 50 ml of tetrahydrofuran was added dropwise under ice cooling. The solid was separated by filtration and extracted with ether. After drying, the ether was evaporated to obtain 28.1 g of 4,4,4-trifluoro-3-tetrahydropyranyloxybutyl alcohol (2) in a purity of 65%. Since the compound (2) was relatively unstable to heat and acid, said compound was only dried in pyridine with a molecular sieve 4A and used in the subsequent step.

Workup

  1. temperatureThe mixture was further refluxed for 30 minutes
  2. customThe solid was separated by filtration
  3. extractionextracted with ether
  4. customAfter drying
  5. customthe ether was evaporated

Sources & evidence

ORD record
ord-2becc26ecd684d9d90275894f7d79676
Source dataset
uspto-grants-1993_11
Patent number
US05264150

Reaction notes

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