Methanol → HCID 58444103, compound

HRID 1892882Notes

Reaction equation

HRID 1892882 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[C:18](=O)[CH:17]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[CH:18]=[C:17]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 4311764Sodium borohydride2×HCID 58444105HCID 58444105, compound

Product 1

HCID 58444103HCID 58444103, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

50 g (150 mmole) 7-(4′-tert-Butyl-phenyl)-2-(2,2-dimethyl-propyl)-indan-1-one were dissolved in 180 ml toluene in a 500 ml—roundbottom flask equipped with a reflux condenser. 6.22 g (1.1 eq.) sodium borohydride were added. Then 26.1 ml (4.3 eq.) methanol were added at 50° C. and the mixture was stirred for 4 h at 50° C. Another 3.11 g sodium borohydride and 10.3 g methanol were added and the mixture was stirred at 50° C. overnight. 2M sulphuric acid was added until the gas evolution ceased. After addition of 100 ml water the layers were separated and the organic layer was washed two times with 2M sulphuric acid and once with a saturated sodium chloride solution. The solvent was evaporated and the crude indanol was dissolved in approx. 300 ml of toluene. After addition of 1 g p-toluene sulfonic acid the mixture was heated to reflux using a Dean-Stark-trap until TLC showed complete conversion (90 min). The solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution. Drying over magnesium sulphate, evaporation of the solvent and recrystallization from 500 ml ethanol afforded 35.3 g (74%) of the desired indene as white crystals. 1H-NMR (400 MHz, CDCl3): δ=7.47 (s, 4H, aromatic), 7.34 (d, 1H, aromatic), 7.25 (d, 1H, aromatic), 7.16 (t, 1H, aromatic), 6.72 (s, 1H, C═CH), 3.44 (s, 2H, benzylic), 2.36 (s, 2H, CH2-t-Bu), 1.37 (s, 9H, Ph-t-Bu), 0.96 (s, 9H, CH2-t-Bu) ppm.

Workup

  1. customequipped with a reflux condenser
  2. stirringthe mixture was stirred at 50° C. overnight
  3. customwere separated
  4. washthe organic layer was washed two times with 2M sulphuric acid
  5. customThe solvent was evaporated
  6. dissolutionthe crude indanol was dissolved in approx. 300 ml of toluene
  7. additionAfter addition of 1 g p-toluene sulfonic acid the mixture
  8. temperaturewas heated
  9. temperatureto reflux
  10. customconversion (90 min)
  11. washThe solution was washed twice with a saturated NaHCO3-solution, once with water and once with a saturated sodium chloride solution
  12. dry with materialDrying over magnesium sulphate, evaporation of the solvent and recrystallization from 500 ml ethanol

Sources & evidence

ORD record
ord-a6f7347c032f4c7c828e1d5f00daa065
Source dataset
uspto-grants-2013_08
Patent number
US08507706B2

Reaction notes

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