Tetrahydrofuran → HCID 68600087, compound

HRID 1951986Notes

Reaction equation

HRID 1951986 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]([Cl:21])[CH:9]=1)(=O)C.[O:22]1CCC[CH2:23]1>>[Cl: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 68601983HCID 68601983, compound

Product 1

HCID 68600087HCID 68600087, compoundYield 77%

Conditions

Temperature
60 °C

Procedure

2.4 g (110 mmol) of lithium borohydride is added in portions to a solution of 10.6 g (36.7 mmol) of [3-chloro-4-(2-methoxy-ethoxymethoxy)-phenyl]-methyl acetate diluted in 110 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 2 hours. The reaction mixture is then poured into 500 ml of ice and then extracted with ethyl acetate. The organic phases are combined, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The solvents are evaporated to give 7.3 g (77%) of 2-[3-chloro-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethanol 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
  6. customThe solvents are evaporated

Sources & evidence

ORD record
ord-5a59e89a49e049acadb75cd2ccd28794
Source dataset
uspto-grants-2013_03
Patent number
US08404836B2

Reaction notes

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