Water → HCID 67632852, compound

HRID 581219Notes

Reaction equation

HRID 581219 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH3:15][N:16]1[CH:20]2[CH2:21][C:22]([CH2:24][CH:17]1[CH2:18][CH2:19]2)=[O:23].O>C(OCC)C>[OH:23][C:22]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])[CH2:21][CH:20]2[N:16]([CH3:15])[CH:17]([CH2:18][CH2:19]2)[CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 113582-BromoanisoleHCID 79038Npc164516HCID 178418339Butyllithium

Product 1

HCID 67632852HCID 67632852, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 2-bromoanisole (9.25 ml, 0.074 mol) in dry diethyl ether (110 ml) under argon was cooled to 0° C. and was treated with n-butyllithium (1.6M) (45.6 ml, 0.073 mol) slowly. The reaction mixture was then allowed to warm to room temp. After 0.5 h, a solution of tropinone (10.14 g, 0.073 mol) in dry diethyl ether (60 ml) was added causing the reaction mixture to reflux. Reflux was maintained for a further 0.5 h, before the reaction mixture was allowed to cool. Water (40 ml) was then added and the reaction mixture was stirred for 0.25 h. The organic layer was then separated, dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow oily solid, which was triturated with petroleum ether (60-80). The resultant suspension was then filtered to give the title compound as a white solid, which was dried in vacuo (9.04 g, 50%).

Workup

  1. temperatureto reflux
  2. temperatureReflux
  3. temperaturewas maintained for a further 0.5 h, before the reaction mixture
  4. temperatureto cool
  5. customThe organic layer was then separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customto give a pale yellow oily solid, which
  9. customwas triturated with petroleum ether (60-80)
  10. filtrationThe resultant suspension was then filtered

Sources & evidence

ORD record
ord-dc4bfa29f8404529a8ce12a2e78cee35
Source dataset
uspto-grants-1999_07
Patent number
US05919932

Reaction notes

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