Tetrahydrofuran → 4-(Tetrahydropyran-2-yloxy)phenylethanol

HRID 1579046Notes

Reaction equation

HRID 1579046 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](OC)=O)=[CH:10][CH:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:25]1CCCC1>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:25])[CH3:15])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 21557782Methyl 4-(tetrahydropyran-2-yloxy)phenylacetate

Product 1

HCID 539473164-(Tetrahydropyran-2-yloxy)phenylethanol

Procedure

A solution of 57 g. of methyl 4-(tetrahydropyran-2-yloxy)phenylacetate, in 2 l. of anhydrous tetrahydrofuran is added dropwise, over a 30 minute period to a stirred suspension of 20 g. of lithium aluminum hydride in 1 l. of anhydrous tetrahydrofuran, under nitrogen atmosphere. The mixture is refluxed for 90 minutes, cooled and cautiously treated with 20 ml. of ethyl acetate, to destroy the excess reagent. Solid sodium sulfate is added, the inorganic material filtered off and thoroughly washed with hot ethyl acetate. Upon evaporation of the combined organic filtrates there is obtained 4-(tetrahydropyran-2-yloxy)phenylethanol.

Workup

  1. temperatureThe mixture is refluxed for 90 minutes
  2. temperaturecooled
  3. additioncautiously treated with 20 ml
  4. customof ethyl acetate, to destroy the excess reagent
  5. additionSolid sodium sulfate is added
  6. filtrationthe inorganic material filtered off
  7. washthoroughly washed with hot ethyl acetate
  8. customUpon evaporation of the combined organic filtrates there

Sources & evidence

ORD record
ord-8e637c9a99154366912be725eb4bdf22
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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