Methyl iodide → HCID 20037276, compound

HRID 1904543Notes

Reaction equation

HRID 1904543 reaction equation
C([O:8][C:9]1[CH:21]=[CH:20][C:12]2[C:13](=[O:19])[CH2:14][C:15]([CH3:18])([CH3:17])[O:16][C:11]=2[CH:10]=1)C1C=CC=CC=1.[BH4-].[Na+].[H-].[Na+].[H][H].[CH3:28]I>CO.O1CCCC1>[CH3:17][C:15]1([CH3:18])[CH2:14][CH:13]([O:19][CH3:28])[C:12]2[CH:20]=[CH:21][C:9]([OH:8])=[CH:10][C:11]=2[O:16]1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4311764Sodium borohydrideHCID 156096367-Benzyloxy-2,3-dihydro-2,2-dimethyl-4-oxobenzopyranHCID 178418361HCID 178418361, compound

Product 1

HCID 20037276HCID 20037276, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7-Benzyloxy-2,3-dihydro-2,2-dimethyl-4-oxobenzopyran synthesized as in Referential Example 22 was dissolved in 60 ml of methanol, and reduced with 1.0 g of sodium borohydride at room temperature. The product was dissolved in 10 ml of tetrahydrofuran, and the solution was added dropwise to a mixture of 1.0 g of 60% sodium hydride and 5 ml of tetrahydrofuran. After generation of hydrogen ceased, 4.3 g of methyl iodide was added dropwise, and the mixture was further stirred for 2.5 hours at room temperature. The reaction mixture was extracted with ethyl acetate. The extract was concentrated, and the residue was dossolved in 30 ml of ethanol and hydrogenated at room temperature for 8 hours in the presence of 5% palladium-carbon catalyst. The crude product was purified by column chromatography to give 2.2 g (yield 58%) of the desired product as a pale brown liquid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated
  3. waitthe residue was dossolved in 30 ml of ethanol and hydrogenated at room temperature for 8 hours in the presence of 5% palladium-carbon catalyst
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7553d45a36b3495eab19d67e82c60f6d
Source dataset
uspto-grants-1989_06
Patent number
US04838924

Reaction notes

Loading…