Sodium Bisulfate → HCID 22664982, compound

HRID 392589Notes

Reaction equation

HRID 392589 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O[C:8]1([CH2:14][C:15]2([C:20]([O:22]CC)=O)[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1.[OH:25]S([O-])(=O)=O.[Na+]>CCOCC>[OH:25][CH:14]([C:15]1([CH2:20][OH:22])[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 69529432HCID 69529432, compound

Product 1

HCID 22664982HCID 22664982, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-20 °C

Procedure

Lithium aluminum hydride (1.05 g, 27.6 mmol) was suspended in ether (80 ml) and the mixture was cooled to −20° C. to −30° C. Thereto was added dropwise a solution of ethyl 1-(1-hydroxyphenylmethyl)cyclopentanecarboxylate (14.118.4 mmol) in ether (10 ml) while maintaining the solution at not higher than −20° C. The mixture was stirred at −20° C. for 1 h and at room temperature for 3 h, cooled to −20° C. and 10% NaHSO4 aqueous solution (40 ml) was added dropwise. The mixture was stirred at 0° C. for 30 min and an insoluble material was removed by decantation. This was washed twice with ether (100 ml), and the organic layer was combined, washed with water and dried over anhydrous sodium sulfate. This was concentrated to dryness to give a colorless oil (3.12 g).

Workup

  1. temperaturethe mixture was cooled to −20° C. to −30° C
  2. temperaturecooled to −20° C.
  3. stirringThe mixture was stirred at 0° C. for 30 min
  4. customan insoluble material was removed by decantation
  5. washThis was washed twice with ether (100 ml)
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationThis was concentrated to dryness

Sources & evidence

ORD record
ord-90ec70df9e89471c85b7651993df0eb7
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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