Hydrochloric Acid → HCID 23286583, compound

HRID 1739533Notes

Reaction equation

HRID 1739533 reaction equation
[CH3:1][CH:2]1[C:10](=O)[C:9]2[CH:8]=[C:7]3[C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:6]3=[CH:5][C:4]=2[CH2:3]1.[BH4-].[Na+].C(O)C.Cl>C(OCC)C>[CH3:1][C:2]1[CH2:10][C:9]2[CH:8]=[C:7]3[C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][C:15]([CH3:17])([CH3:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 19350458HCID 19350458, compound

Product 1

HCID 23286583HCID 23286583, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2,3,5,7-Tetrahydro-2,5,5,8,8-pentamethyl-1H-Benz(f)inden-1-one (14.89 g, 58.08 mmol) and NaBH4 (2.21 g, 58.5 mmol) were stirred in diethylether (200 mL) at 0° C. as ethanol (100 mL) was added slowly. This mixture was allowed to warm slowly to room temperature and then stirred at room temperature overnight. After the reaction period the mixture was poured onto crushed ice and made acidic with HCl. The organic layer was then separated and washed with 1M HCl (1×100 mL). The volatiles were then removed from the organic layer and the residue refluxed in benzene (300 mL) with ptoluenesulfonic acid (0.12 g) using a Dean-Stark apparatus until no more H2O was evolved. The mixture was then washed with 1 M NaHCO3 (2×100 mL) and the volatiles were removed from the organic layer resulting in the isolation of a yellow oil. Recrystallization from MeOH (0° C.) gave the desired product as off-white crystals (10.37 g, 74.3 percent yield).

Workup

  1. additionwas added slowly
  2. customAfter the reaction period the mixture
  3. additionwas poured
  4. customonto crushed ice
  5. customThe organic layer was then separated
  6. washwashed with 1M HCl (1×100 mL)
  7. customThe volatiles were then removed from the organic layer
  8. temperaturethe residue refluxed in benzene (300 mL) with ptoluenesulfonic acid (0.12 g)
  9. washThe mixture was then washed with 1 M NaHCO3 (2×100 mL)
  10. customthe volatiles were removed from the organic layer
  11. customresulting in the isolation of a yellow oil
  12. customRecrystallization from MeOH (0° C.)

Sources & evidence

ORD record
ord-46ef14ef03d44619b340acbfd867ee61
Source dataset
uspto-grants-1999_10
Patent number
US05965756

Reaction notes

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