Water → 1H-Indene, (1-methylethyl)-

HRID 979173Notes

Reaction equation

HRID 979173 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.BrC(C)C.O>C(OCC)C>[CH:2]([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 7219IndeneHCID 178418339Butyllithium

Product 1

HCID 2364061H-Indene, (1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyl lithium (37 ml in hexane) was added to a solution of 1H-indene (6.30 ml) in anhydrous diethyl ether (40 ml) under nitrogen atmosphere at 15° C. The solution was stirred at room temperature for 10 min, 2-bromopropane (18.8 g) in anhydrous ether (100 ml) was added, and stirring was continued for 72 hours. Water (30 ml) was added, the phases were separated, and the aqueous phase was extracted with ether. The combined ether solutions was washed with water, dried (MgSO4) and condensed. The residue was distilled (50°-55° C., 0.03 mmHg) to give 1-isopropyl-1H-indene (5.95 g).

Workup

  1. stirringstirring
  2. waitwas continued for 72 hours
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ether
  5. washThe combined ether solutions was washed with water
  6. customdried
  7. custom(MgSO4) and condensed
  8. distillationThe residue was distilled (50°-55° C., 0.03 mmHg)

Sources & evidence

ORD record
ord-5d9ce944e80a4f8da85d41b704e996b3
Source dataset
uspto-grants-1987_05
Patent number
US04666925

Reaction notes

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