Hydrochloric Acid → HCID 67985115, compound

HRID 1525468Notes

Reaction equation

HRID 1525468 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]2=O)=[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]=1[O:25][CH3:26])([CH3:4])([CH3:3])[CH3:2].CO.[BH4-].[Na+].Cl>C1COCC1>[C:1]([C:5]1[CH:13]=[C:12]2[C:8](=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]=1[O:25][CH3:26])[CH2:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 67982916HCID 67982916, compound

Product 1

HCID 67985115HCID 67985115, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.0 g (25.7 mmol) of 6-tert-butyl-2-isobutyl-5-methoxy-4-phenylindan-1-one in 100 ml of THF and 50 ml of methanol 10.0 g (0.265 mol) of NaBH4 was added by small portions by vigorous stirring for ca. 1.5 h at room temperature. This mixture was additionally stirred overnight and then acidified by 2 M HCl to pH 1. The product was extracted with 3×150 ml of dichloromethane. The organic extract was evaporated to dryness, and a mixture of the residue with 150 ml of toluene and 0.5 g of TsOH was refluxed for 15 min using Dean-Stark head. The obtained solution was washed by 10% aqueous K2CO3. The organic layer was separated, and the aqueous layer was extracted with 2×50 ml of dichloromethane. The combined organic extract was dried over K2CO3, evaporated to dryness, and then passed through short layer of silica gel 60 (40-63 um). The silica gel layer was additionally washed by hexanes-dichloromethane (1:1, vol.). The elute was evaporated to dryness, and the residue was dried in vacuum. This procedure gave 8.52 g (99%) of yellowish oil of the title product which was further used without an additional purification.

Workup

  1. waitThis mixture was additionally stirred overnight
  2. extractionThe product was extracted with 3×150 ml of dichloromethane
  3. extractionThe organic extract
  4. customwas evaporated to dryness
  5. additiona mixture of the residue with 150 ml of toluene and 0.5 g of TsOH
  6. temperaturewas refluxed for 15 min
  7. washThe obtained solution was washed by 10% aqueous K2CO3
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with 2×50 ml of dichloromethane
  10. extractionThe combined organic extract
  11. dry with materialwas dried over K2CO3
  12. customevaporated to dryness
  13. washThe silica gel layer was additionally washed by hexanes-dichloromethane (1:1, vol.)
  14. customThe elute was evaporated to dryness
  15. customthe residue was dried in vacuum

Sources & evidence

ORD record
ord-dd52a8140fa54e37b130e28ad106b252
Source dataset
uspto-grants-2015_07
Patent number
US09079985B2

Reaction notes

Loading…