Tetrahydrofuran → HCID 68601229, compound

HRID 1951984Notes

Reaction equation

HRID 1951984 reaction equation
[BH4-].[Li+].C(O[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:10]([F:21])[CH:9]=1)(=O)C.[O:22]1CCC[CH2:23]1>>[F:21][C:10]1[CH:9]=[C:8]([CH2:7][CH2:23][OH:22])[CH:13]=[CH:12][C:11]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 68600580HCID 68600580, compound

Product 1

HCID 68601229HCID 68601229, compoundYield 99%

Conditions

Temperature
60 °C

Procedure

2.4 g (107 mmol) of lithium borohydride is added in portions to a solution of 9.7 g (36 mmol) of [3-fluoro-4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 1.5 h and then it is poured into 500 ml of ice and extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. 8.6 g (99%) of 2-[3-fluoro-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethanol is obtained in the form of a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-67e74727261547c3b2d6ceb447d3a5d9
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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