Acetone → HCID 18947763, compound

HRID 1769312Notes

Reaction equation

HRID 1769312 reaction equation
[BH4-].[Na+].CC(C)=O.C(Cl)Cl.Cl.[S:11]1[CH:15]=[CH:14][C:13]2[CH:16]=[C:17]([CH:20]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[C:21](OC)=[O:22])[CH:18]=[CH:19][C:12]1=2>C(O)C.O>[S:11]1[CH:15]=[CH:14][C:13]2[CH:16]=[C:17]([CH:20]([O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)[CH2:21][OH:22])[CH:18]=[CH:19][C:12]1=2

Participants

8

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydride2×HCID 53904631HCID 53904631, compound

Product 1

HCID 18947763HCID 18947763, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

In 41.3 ml of ethanol was dissolved the methyl (-)-2-(benzo[b]thiophen-5-yl)-2-(tetrahydropyranyloxy)acetate, and to this solution was added 2.90 g of sodium borohydride, and the resulting mixture was stirred at 25° C. for 8 hours. Subsequently, 13.23 ml of acetone was 1 dropwise added with ice-cooling to decompose the excessive sodium borohydride, and thereafter, 138 ml of methylene chloride and 138 ml of water were added thereto, and the pH was adjusted to 8.5 with 2N hydrochloric acid. The organic layer formed was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue thus obtained was washed with petroleum ether to obtain 12.0 g (yield: 96%) of colorless (-)-2-(benzo[b]thiophen-5-yl)-2-(tetrahydropyranyloxy)ethanol as a diastereomer mixture.

Workup

  1. additiondropwise added with ice-
  2. temperaturecooling
  3. customThe organic layer formed
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue thus obtained
  9. washwas washed with petroleum ether

Sources & evidence

ORD record
ord-687d40b89b7f4b24a93ca60644f3bbc4
Source dataset
uspto-grants-1995_01
Patent number
US05380878

Reaction notes

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