Methanol → HCID 71231030, compound

HRID 716476Notes

Reaction equation

HRID 716476 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH3:15])[C:11]2=O)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]=1[O:22][CH2:23][CH:24]([CH3:26])[CH3:25])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:13]=[C:12]2[C:8](=[C:7]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:6]=1[O:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:9][C:10]([CH3:15])=[CH:11]2)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 71230807HCID 71230807, compound

Product 1

HCID 71231030HCID 71231030, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 34.0 g (97.0 mmol) of 6-tert-butyl-5-isobutoxy-2-methyl-4-phenylindan-1-one in 300 ml of THF cooled to 5° C. 5.00 g (132 mmol) of NaBH4 was added. Further on, 150 ml of methanol was added dropwise to this mixture by vigorous stirring for ca. 7 h at 5° C. The resulting mixture was evaporated to dryness, and the residue was partitioned between 500 ml of dichloromethane and 500 ml of 1 M HCl. The organic layer was separated, the aqueous layer was additionally extracted with 100 ml of dichloromethane. The combined organic extract was evaporated to dryness to give a colorless oil. To a solution of this oil in 500 ml of toluene 1 g of TsOH was added, and this mixture was refluxed with Dean-Stark head for 15 min and then cooled to room temperature using a water bath. The resulting solution was washed by 10% aqueous Na2CO3. The organic layer was separated, the aqueous layer was extracted with 2×100 ml of dichloromethane. The combined organic solution was dried over K2CO3 and then passed through a short pad of silica gel 60 (40-63 um). The silica gel pad was additionally washed by 100 ml of dichloromethane. The combined organic elute was evaporated to dryness. This procedure gave 32.4 g (99%) of 5-tert-butyl-6-isobutoxy-2-methyl-7-phenyl-1H-indene which was further used without an additional purification.

Workup

  1. customThe resulting mixture was evaporated to dryness
  2. customthe residue was partitioned between 500 ml of dichloromethane and 500 ml of 1 M HCl
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was additionally extracted with 100 ml of dichloromethane
  5. extractionThe combined organic extract
  6. customwas evaporated to dryness
  7. customto give a colorless oil
  8. temperaturethis mixture was refluxed with Dean-Stark head for 15 min
  9. temperaturecooled to room temperature
  10. washThe resulting solution was washed by 10% aqueous Na2CO3
  11. customThe organic layer was separated
  12. extractionthe aqueous layer was extracted with 2×100 ml of dichloromethane
  13. dry with materialThe combined organic solution was dried over K2CO3
  14. washThe silica gel pad was additionally washed by 100 ml of dichloromethane
  15. washThe combined organic elute
  16. customwas evaporated to dryness

Sources & evidence

ORD record
ord-25004e9f6ad94210a9ea6407d833cf04
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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