Water → [1-(4-Ethoxyphenyl)-2,2-difluorocyclopropyl]methanol

HRID 6501Notes

Reaction equation

HRID 6501 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][CH:18]=2)[CH2:14][C:13]1([F:16])[F:15])=O)C.O.[OH-].[Na+]>CCOCC>[CH2:24]([O:23][C:20]1[CH:19]=[CH:18][C:17]([C:12]2([CH2:10][OH:9])[CH2:14][C:13]2([F:15])[F:16])=[CH:22][CH:21]=1)[CH3:25]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 6454760Ethyl 1-(4-ethoxyphenyl)-2,2-difluorocyclopropane-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 14346307[1-(4-Ethoxyphenyl)-2,2-difluorocyclopropyl]methanolYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 1.0 g of lithium aluminium hydride in 120 ml of dry ether, at room temperature is added dropwise 5.4 g (0.02 moles) of ethyl-1-(4-ethoxyphenyl)-2,2-difluorocyclopropane-1-carboxylate in 20 ml of ether. The reaction mixture is stirred for 1 hr after which 1.0 ml of water 1.0 ml of 15% NaOH, followed by 3.0 ml of water are added. The solid precipitate is filtered off, washed with ether and the combined filtrates dried and concentrated under reduced pressure to yield (4.2 g) a colourless oil; nD 1.5129

Workup

  1. additionare added
  2. filtrationThe solid precipitate is filtered off
  3. washwashed with ether
  4. customthe combined filtrates dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24c621edc5884c249b64914319a77e74
Source dataset
uspto-grants-1993_09
Patent number
US05248834

Reaction notes

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