1,2-Dibromoethane → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-hydroxytetrahydrothiophene

HRID 1736491Notes

Reaction equation

HRID 1736491 reaction equation
[Mg].BrCCBr.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1.[S:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]1.[Cl-].[NH4+]>O1CCCC1>[CH:16]1([O:15][C:9]2[CH:8]=[C:7]([C:23]3([OH:26])[CH2:24][CH2:25][S:21][CH2:22]3)[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 61252Dihydro-3(2H)-thiophenoneHCID 5462224MagnesiumHCID 99703924-Bromo-2-(cyclopentyloxy)-1-methoxybenzene

Product 1

HCID 194331153-(3-Cyclopentyloxy-4-methoxyphenyl)-3-hydroxytetrahydrothiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirring suspension of magnesium turnings (3.45 g) in dry tetrahydrofuran (60 mL) is treated with 1,2-dibromoethane (0.8 mL), and the mixture is stirred under a nitrogen atmosphere for 30 minutes. It is then treated dropwise with a solution of 4-bromo-2-cyclopentyloxyanisole (25 g); which is prepared as described in Reference Example 4 in tetrahydrofuran (20 mL), and the resulting solution is heated at reflux for 30 minutes. The solution is then cooled to room temperature and treated with a solution of tetrahydrothiophen-3-one (6.9 mL) in tetrahydrofuran (20 mL), and allowed to stand for 16 hours. It is then treated with saturated aqueous ammonium chloride solution (50 mL), and the mixture is partitioned between water (100 mL) and dichloromethane (100 mL). The aqueous phase is further extracted with dichloromethane (100 mL). The combined organic phases are dried over magnesium sulphate and evaporated. The resulting residue is subjected to flash chromatography on silica gel, using a mixture of ethyl acetate and toluene as eluent to give 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-hydroxytetrahydrothiophene, in the form of a viscous oil.

Workup

  1. customwhich is prepared
  2. temperaturethe resulting solution is heated
  3. temperatureat reflux for 30 minutes
  4. waitto stand for 16 hours
  5. customthe mixture is partitioned between water (100 mL) and dichloromethane (100 mL)
  6. extractionThe aqueous phase is further extracted with dichloromethane (100 mL)
  7. dry with materialThe combined organic phases are dried over magnesium sulphate
  8. customevaporated
  9. additiona mixture of ethyl acetate and toluene as eluent

Sources & evidence

ORD record
ord-9b2a24d6866a4428846e1a94efda8ea6
Source dataset
uspto-grants-1996_07
Patent number
US05541219

Reaction notes

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