Potassium Carbonate → HCID 69881937, compound

HRID 1602699Notes

Reaction equation

HRID 1602699 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]3([CH3:19])[CH:13]4[CH2:17][C:16]([CH3:18])([C:10]3([CH3:20])[C:9]=2[CH:21]=1)[CH2:15][CH2:14]4)=[O:4].[OH:22][C:23]1[CH:24]=[C:25]([CH:30]=[CH:31][C:32]=1[I:33])[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:18][C:16]12[CH2:17][CH:13]([C:11]3([CH3:19])[C:10]1([CH3:20])[C:9]1[CH:21]=[C:5]([C:3]([CH2:2][O:22][C:23]4[CH:24]=[C:25]([CH:30]=[CH:31][C:32]=4[I:33])[C:26]([O:28][CH3:29])=[O:27])=[O:4])[CH:6]=[CH:7][C:8]=1[O:12]3)[CH2:14][CH2:15]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoateHCID 86594054HCID 86594054, compound

Product 1

HCID 69881937HCID 69881937, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-1,4a,9b-trimethyl-1,4-methanodibenzofur-8-yl bromomethyl ketone (2.5 g, 6.86 mmol), methyl 3-hydroxy-4-iodobenzoate (1.9 g, 6.83 mmol) and potassium carbonate (0.95 g, 6.88 mmol) in methyl ethyl ketone (50 ml) is refluxed for five hours. The reaction medium is filtered, after which 40 ml of water and 40 ml of ethyl ether are added. After stirring and separation of the phases by settling, the organic phase is washed twice with 40 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on a column of silica (30% ethyl acetate, 70% heptane).

Workup

  1. filtrationThe reaction medium is filtered
  2. additionafter which 40 ml of water and 40 ml of ethyl ether are added
  3. customseparation of the phases
  4. washthe organic phase is washed twice with 40 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe product is purified by flash chromatography on a column of silica (30% ethyl acetate, 70% heptane)

Sources & evidence

ORD record
ord-0f9f6b79c5634dcbade5f27c2fe2e18d
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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