Sodium borohydride → 6-tert-butyl-2,3-dihydro-1H-inden-1-ol

HRID 1017148Notes

Reaction equation

HRID 1017148 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 184028836-tert-butyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 184028506-tert-butyl-2,3-dihydro-1H-inden-1-olYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

A 3 L one neck flask fit with an overhead stirrer, condenser, nitrogen inlet, solids addition funnel, and thermometer was charged with crude 6-t-butyl-1-indanone (109 g, 0.577 mol) and anhydrous ethanol (1.5 L). The reaction was heated to 30-40° C. and sodium borohydride (43.6 g, 1.15 mol) was added over the course of 30 min followed by heating to reflux overnight. The next day an additional amount of sodium borohydride is added (12.0 g, 0.32 mol) and reflux continued for an hour. The reaction was cooled, quenched in 5% HCl/ice (1 L), extracted into diethyl ether (1 L), and the organic layer washed with water (14×150 mL), and dried over anhydrous sodium sulfate. Rotary evaporation to remove the solvent gave crude 6-t-butyl-1-indanol (64.4 g). Another diethyl ether extraction as above gave an additional amount of crude 6-t-butyl-1-indanol (75.5 g total). 1HNMR (CDCl3, 500 MHz) δ7.46 (s, 1H); 7.32 (dd, JAB=1.5, 8 Hz, 1H); 7.19 (d, JAB=8 Hz, 1H); 5.24 (t, J=6 Hz); 3.01 (m, 1H); 2.78 (p, J=7.5 Hz, 1H); 2.50 (m, 1H); 1.95 (m, 1H); 1.32 (s, 9H).

Workup

  1. temperatureby heating
  2. temperatureto reflux overnight
  3. temperaturereflux
  4. waitcontinued for an hour
  5. temperatureThe reaction was cooled
  6. customquenched in 5% HCl/ice (1 L)
  7. extractionextracted into diethyl ether (1 L)
  8. washthe organic layer washed with water (14×150 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customRotary evaporation
  11. customto remove the solvent
  12. customgave crude 6-t-butyl-1-indanol (64.4 g)
  13. extractionAnother diethyl ether extraction as

Sources & evidence

ORD record
ord-f988020b5e23410482cf89a84cadc9be
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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