Methyl Ethyl Ketone → (3RS,4RS)-4-[4-(2-chloroethyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochroman

HRID 1859348Notes

Reaction equation

HRID 1859348 reaction equation
C(C(C)=O)C.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=3)[S:16][CH2:15][C:14]2([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH3:27])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][CH2:46][Cl:47]>O>[Cl:47][CH2:46][CH2:45][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][O:25][CH3:26])=[CH:20][CH:21]=3)[S:16][CH2:15][C:14]2([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:32][CH:33]=2)[CH3:27])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 22123581(3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman

Product 1

HCID 22123597(3RS,4RS)-4-[4-(2-chloroethyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochromanYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To methyl ethyl ketone solution (3 ml) of (3RS,4RS)-4-(4-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-thiochroman (126 mg, 0.28 mmol) were added potassium carbonate (96 mg, 0.70 mmol) and 1-bromo-2-chloroethane (115 ml, 1.38 mmol), and the mixture was heated under refluxing for 70 hours. After adding water, the reaction solution was extracted with ethyl acetate. The extract was distilled under reduced pressure to remove the solvent and the crude product thus obtained was then purified using silica gel plate (ethyl acetate:hexane=1:2) to obtain 69 mg (yield: 48%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 70 hours
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. distillationThe extract was distilled under reduced pressure
  5. customto remove the solvent
  6. customthe crude product thus obtained
  7. customwas then purified

Sources & evidence

ORD record
ord-2d0fecaafe9d47449a39e514f8254dfd
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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