Water → HCID 11229784, compound

HRID 855462Notes

Reaction equation

HRID 855462 reaction equation
C([O:3][C:4](=O)[C@H:5]([O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[C:6]1([C@@H:5]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:4][OH:3])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86602781Ethyl (αR)-α-[(tetrahydro-2H-pyran-2-yl)oxy]benzeneacetate

Product 1

HCID 11229784HCID 11229784, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 4 g (15.1 mmole) of (R)-(−)-ethyl-2-phenyl-2-(tetrahydropyranyloxy)acetate (8) in 75 ml of dry ether was added dropwise to a stirred suspension of 1.72 g (45.3 mmole) of lithium aluminium hydride and 50 ml of ether at room temperature. After the addition was completed, the mixture was refluxed for additional 2 h, then cooled in an ice bath, and treated carefully subsequently with 1.72 ml of water, 1.72 ml of 15% sodium hydroxide, and 5.4 ml of water. After being stirred for additional 30 min, the mixture was filtered with suction, and the precipitate (aluminum salts) was washed with ether. The combined ethereal solution was dried over magnesium sulfate, and the solvent was evaporated to leave 3.3 g of a clear oil (97%).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for additional 2 h
  3. temperaturecooled in an ice bath
  4. filtrationthe mixture was filtered with suction
  5. washthe precipitate (aluminum salts) was washed with ether
  6. dry with materialThe combined ethereal solution was dried over magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-250f55c9c9a14c6db4b9b3ad1e1092d2
Source dataset
uspto-grants-2007_08
Patent number
US07261836B2

Reaction notes

Loading…