Water → Tetrahydro-2H-pyran-3-ethanol

HRID 1011065Notes

Reaction equation

HRID 1011065 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[O:12]1[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][C:19](O)=[O:20])[CH2:13]1.O>C1COCC1>[O:12]1[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][CH2:19][OH:20])[CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 229657672-(Oxan-3-yl)acetic acid

Product 1

HCID 55264768Tetrahydro-2H-pyran-3-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride in Et2O (4.16 ml, 4.16 mmol) was added dropwise to a solution of tetrahydro-2H-pyran-3-ylacetic acid (Tet. Lett. 2003, 44, 6355) (0.6 g, 4.16 mmol) in THF (5 ml) at room temperature under nitrogen. The mixture was stirred for 1 hour and was treated very slowly dropwise with water (1 ml). After the reaction was quenched, aqueous sodium hydroxide (2N, 1 ml) was added and the mixture was stirred for 5 min. The suspension was filtered through Hyflo and evaporated to the title compound as a colourless oil (0.3 g).

Workup

  1. customAfter the reaction was quenched
  2. additionaqueous sodium hydroxide (2N, 1 ml) was added
  3. stirringthe mixture was stirred for 5 min
  4. filtrationThe suspension was filtered through Hyflo
  5. customevaporated to the title compound as a colourless oil (0.3 g)

Sources & evidence

ORD record
ord-806f6925d9ff4c9fabc0cb06cc50e9bf
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…