Ethyl tetrahydropyran-4-ylacetate → 2-(Oxan-4-yl)ethan-1-ol

HRID 227374

Reaction equation

HRID 227374 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8]1>O1CCCC1>[O:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][OH:15])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 2773412Ethyl tetrahydropyran-4-ylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 177509442-(Oxan-4-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 15 mL of tetrahydrofuran (THF) at 0° C. was added LiAlH4 (0.28 g, 7.3 mmol). This mixture was stirred for 10 min then the ethyl tetrahydropyran-4-yl-acetate (Combi-Blocks Inc., 0.50 g, 2.9 mmol) was added. The reaction was stirred for 5 min at 0° C. then was allowed to warm to ambient temperature and was stirred for 90 min. The reaction was quenched with excess NaHSO4.10H2O and was stirred for 60 min. The mixture was filtered through Celite. The filtrate was concentrated to give the title compound which was carried on without further purification. MS (DCI/NH3) m/z 131 (M+H)+.

Workup

  1. stirringThe reaction was stirred for 5 min at 0° C.
  2. stirringwas stirred for 90 min
  3. customThe reaction was quenched with excess NaHSO4.10H2O
  4. stirringwas stirred for 60 min
  5. filtrationThe mixture was filtered through Celite
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5976d4588e174b91ab708aed313d55d1
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Linked notes

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