Hydrochloric Acid → HCID 67984570, compound

HRID 1525473Notes

Reaction equation

HRID 1525473 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]2=O)=[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]=1[O:26][CH3:27])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C1COCC1.Cl>O>[C:1]([C:5]1[CH:13]=[C:12]2[C:8](=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]=1[O:26][CH3:27])[CH2:9][C:10]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:11]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 67983020HCID 67983020, compound

Product 1

HCID 67984570HCID 67984570, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

To a mixture of 19.7 g of 6-tert-butyl-2-(2,2-dimethylpropyl)-5-methoxy-4-phenyl-1-indanone of 93% purity (50.3 mmol), 15.0 g of NaBH4, and 200 ml of THF 100 ml of water was slowly (for ca. 10 h) added by vigorous stirring at 5° C. The resulting mixture was stirred overnight at room temperature. Further on, 500 ml of cold water was added, the resulting mixture was acidified by 12 N HCl to pH 1, and then the crude product was extracted with 3×150 ml of dichloromethane. To a solution of the residue in 300 ml of toluene 0.5 g of TsOH was added, the resulting mixture was refluxed for 15 min with Dean-Stark head, then quickly cooled to room temperature, and treated with 50 ml of 10% aqueous K2CO3 to remove acidic impurities. The organic layer was separated, the aqueous layer was extracted with 2×75 ml of dichloromethane. The combined organic extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-64 um, 450 m3 of silica gel, eluent: hexanes-dichloromethane=4:1, vol.). Yield 17.3 g (99%) of the title product as yellowish oil.

Workup

  1. custom(for ca. 10 h)
  2. additionadded
  3. stirringThe resulting mixture was stirred overnight at room temperature
  4. extractionthe crude product was extracted with 3×150 ml of dichloromethane
  5. additionTo a solution of the residue in 300 ml of toluene 0.5 g of TsOH was added
  6. temperaturethe resulting mixture was refluxed for 15 min with Dean-Stark head
  7. temperaturequickly cooled to room temperature
  8. additiontreated with 50 ml of 10% aqueous K2CO3
  9. customto remove acidic impurities
  10. customThe organic layer was separated
  11. extractionthe aqueous layer was extracted with 2×75 ml of dichloromethane
  12. extractionThe combined organic extract
  13. dry with materialwas dried over K2CO3
  14. customevaporated to dryness
  15. customThe product was isolated by flash-chromatography on silica gel 60 (40-64 um, 450 m3 of silica gel, eluent: hexanes-dichloromethane=4:1, vol.)

Sources & evidence

ORD record
ord-1f7364abee6f4fde92b3753185cf23e5
Source dataset
uspto-grants-2015_07
Patent number
US09079985B2

Reaction notes

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