Carbon Dioxide → HCID 18786121, compound

HRID 1107876Notes

Reaction equation

HRID 1107876 reaction equation
CC(C[AlH]CC(C)C)C.C(=O)=O.C([O:15][C:16]([C:18]1[O:19][C:20]2[C:27]([Br:28])=[CH:26][CH:25]=[CH:24][C:21]=2[C:22]=1[CH3:23])=O)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O.CC(C)=O>[OH:15][CH2:16][C:18]1[O:19][C:20]2[C:27]([Br:28])=[CH:26][CH:25]=[CH:24][C:21]=2[C:22]=1[CH3:23]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 18786129HCID 18786129, compound

Product 1

HCID 18786121HCID 18786121, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

51.82 ml of a 1.5 molar solution of DIBAL-H in toluene are added dropwise to a solution, cooled to -78° C. with a bath of solid carbon dioxide and acetone, of 10 g (35.3 mmol) of 2-ethyloxycarbonyl-3-methyl-7-bromobenzofuran in 100 ml of toluene. The solution is allowed to return to room temperature and 50 ml of water and 100 ml of a saturated solution of Rochelle salt are successively added. Extraction is carried out with ethyl acetate (3×80 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 2% methanol in dichloromethane). 6.3 g (Yield: 74%) of 2-hydroxymethyl-3-methyl-7-bromobenzofuran are obtained--M.p.: 103° C.

Workup

  1. customto return to room temperature
  2. extractionExtraction
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified by silica column chromatography (elution solvent: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1a0741a4aa9543c9b0cbcb2c0e48e59d
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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