Indene → HCID 70015779, compound

HRID 412511Notes

Reaction equation

HRID 412511 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Li])CCC.[CH:15]12[O:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20]2.[Cl-].[NH4+]>CCCCCC>[CH:1]1([C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[OH:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 7219IndeneHCID 9246Cyclohexene oxideHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 70015779HCID 70015779, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of 29.4 g of indene (0.25 mol) in 500 mL of dry hexane was reacted with 100 mL of n-butyllithium (2.5M in hexanes, 0.25 mol) at room temperature. After 2 hrs. the slurry was chilled in ice water and a solution of 24.5 g of cyclohexene oxide (0.25 mol) in 200 mL of dry hexane added during 8 hrs. After warming to room temperature the slurry was stirred overnight. The resulting mixture was treated with aqueous ammonium chloride and the resulting organic layer was separated and washed with water and then with brine. After drying over sodium sulfate, the solution was evaporated to yield 47 g of crude title compound. Purification was achieved by chromatographing in two portions using 250 g of silica gel, eluting initially with 9:1 hexane:ethyl acetate and ultimately with 2:1 hexane:ethyl acetate. The total yield of purified trans-2-(1-indenyl)-cyclohexanol was 20.0 g (0.0935 mol, 37% yield based on indene). 1H NMR (500 MHz, apparent coupling constant in Hz, CDCl3) δ7.48 (1H, m), 7.46 (1H, m), 7.29 (1H, tm, J=7.6), 7.21 (1H, td, J=7.6, 1.2), 6.34 (1H, t, 0.8), 3.84 (1H, td, J=9.89, 4.4), 3.37 (2H, m), 2.63 (1H, m), 2.14 (1H, m), 1.98 (1H, dm, J=13.4), 1.92 (1H, br s), 1.86 (1H, m), 1.76 (1H, dm, J=12.0), 1.5-1.3 (4H, m).

Workup

  1. customthe resulting organic layer was separated
  2. washwashed with water
  3. dry with materialAfter drying over sodium sulfate
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-bd7bf9d855f146d58f41a3a04476e498
Source dataset
uspto-grants-2003_05
Patent number
US06562921B1

Reaction notes

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