Chloride → HCID 18314122, compound

HRID 277183Notes

Reaction equation

HRID 277183 reaction equation
CS(C)=O.[Cl-].[OH:6][CH2:7][C:8]1[C:17]([CH2:18][O:19][CH3:20])=[CH:16][C:15]2[C:14]([CH3:22])([CH3:21])[CH2:13][CH2:12][C:11]([CH3:24])([CH3:23])[C:10]=2[CH:9]=1.C(N(CC)CC)C>ClCCl.O>[CH3:20][O:19][CH2:18][C:17]1[C:8]([CH:7]=[O:6])=[CH:9][C:10]2[C:11]([CH3:24])([CH3:23])[CH2:12][CH2:13][C:14]([CH3:22])([CH3:21])[C:15]=2[CH:16]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 18314128HCID 18314128, compound

Product 1

HCID 18314122HCID 18314122, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.321 ml dimethyl sulfoxide was added to 5 ml solution of 0.198 ml oxazalyl chloride in dichloromethane at −78° C., and the mixture was stirred at the same temperature for 5 minutes. 2 ml solution of 290 mg 2-hydroxymethyl-3-methoxymethyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene in dichloromethane was added to the mixture at −78° C., and the mixture was further stirred at the same temperature for 40 minutes. After 0.946 ml triethylamine was added to the reaction mixture at −78° C., the temperature was raised to room temperature over 45 minutes. After water was added thereto, the reaction solution was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. Then, the residue obtained under reduced pressure was subjected to silica gel column chromatography to give 190 mg of the title compound as a yellow oil.

Workup

  1. stirringthe mixture was further stirred at the same temperature for 40 minutes
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThen, the residue obtained under reduced pressure

Sources & evidence

ORD record
ord-93ba86c96071462a896bf16e05840f0f
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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