Hydrochloric Acid → HCID 69036788, compound

HRID 1786522Notes

Reaction equation

HRID 1786522 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:16][C:11]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:10][C:9](=[O:17])[C:8]=2[CH:18]=1.Cl>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:16][C:11]3([CH2:12][CH2:13][CH2:14][CH2:15]3)[CH2:10][CH:9]([OH:17])[C:8]=2[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 591678716-Bromospiro[2H-1-benzopyran-2,1′-cyclopentan]-4(3H)-one

Product 1

HCID 69036788HCID 69036788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4.65 g, 0.123 mol) was added to a stirred suspension of 6-bromo-3,4-dihydro-spiro[2H-1-benzopyran-2,1′-cyclopentan]-4-one (31.83 g, 0.1137 mol) in methanol (650 mL) at 0° C. and the mixture was maintained at this temperature for a further 30 minutes. After stirring for an additional 30 minutes at room temperature, concentrated hydrochloric acid was added until acid and the solvent was evaporated under reduced pressure. Water was added to the residue and the product was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The crude product was recrystallized from diethylether/petroleum ether 40-60° C. (⅓). The resulting precipitate was collected by filtration, washed with petroleum ether and dried (71%). mp: 123-123.5° C., IR (KBr): 3271 (O—H), 2963, 2873 (C—H aliphatic) cm−1, Anal. (C13H15O2Br) C, H.

Workup

  1. temperaturethe mixture was maintained at this temperature for a further 30 minutes
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe crude product was recrystallized from diethylether/petroleum ether 40-60° C. (⅓)
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with petroleum ether
  10. customdried (71%)

Sources & evidence

ORD record
ord-f0f4ba2f76c247f393accfad4465076f
Source dataset
uspto-grants-2009_03
Patent number
US07507761B2

Reaction notes

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