Ethylene Oxide → 2-(1H-Inden-1-yl)ethan-1-ol

HRID 442055Notes

Reaction equation

HRID 442055 reaction equation
C([Li])CCC.[Li].C(Br)CCC.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.[CH2:21]1[O:23][CH2:22]1>CCOCC.O>[CH:12]1([CH2:21][CH2:22][OH:23])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

8

Reactant 5

HCID 6354Ethylene OxideHCID 7219IndeneHCID 8002Butyl bromideHCID 3028194Lithium2×HCID 178418339Butyllithium

Product 1

HCID 232887512-(1H-Inden-1-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

The above compound is prepared as described by Howell & Taylor, J.C.S., 1957, 3013. To butyl-lithium, prepared from lithium (20.0 g.) and butyl bromide (234 g.) in ether, indene (116 g., 1.0 M) is added with stirring under nitrogen at -10°. After 1 hour at -10° ethylene oxide (88 g.) in ether (300 ml.) is added in 1/2 hour. After warming to 10°, 500 ml. water is added cautiously and stirring is continued until there is no lithium remaining. The layers are separated and the organic layer is washed once with dilute HCl and three times with water. After drying, the ether is removed and the product distilled, collecting 76 g. (48%) at 125-135/0.2 mm. N.M.R. establishes the position of the double bond as 2,3.

Workup

  1. customThe above compound is prepared
  2. additionis added
  3. temperatureAfter warming to 10°
  4. stirringstirring
  5. customThe layers are separated
  6. washthe organic layer is washed once with dilute HCl and three times with water
  7. customAfter drying
  8. customthe ether is removed
  9. distillationthe product distilled
  10. customcollecting 76 g

Sources & evidence

ORD record
ord-d910e172e2834b1eb6fc2a00706bb311
Source dataset
uspto-grants-1977_08
Patent number
US04044040

Reaction notes

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