Hydrochloric Acid → 4-(2,4-Bis(methoxymethoxy)phenyl)tetrahydrothio-pyran-4-ol

HRID 386845Notes

Reaction equation

HRID 386845 reaction equation
CN(C)[CH2:3][CH2:4]N(C)C.Br[C:10]1C=C[C:13]([O:16][CH2:17][O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH2:21][O:22][CH3:23].C([Li])CCC.[S:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1.Cl.[O:37]1CCCC1>CCCCCC>[CH3:19][O:18][CH2:17][O:16][C:13]1[CH:12]=[C:11]([O:20][CH2:21][O:22][CH3:23])[CH:10]=[CH:33][C:34]=1[S:29][C:30]1([OH:37])[CH2:31][CH2:32][O:35][CH2:4][CH2:3]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 66173Tetrahydrothiopyran-4-oneHCID 113917541-Bromo-2,4-bis(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 667451594-(2,4-Bis(methoxymethoxy)phenyl)tetrahydrothio-pyran-4-ol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

6.35 ml of tetramethylethylenediamine are added to a solution of 5.54 g of 1-bromo-2,4-bis(methoxy-methoxy)benzene in 80 ml of tetrahydrofuran. The mixture is cooled to −70° C. and 16.8 ml of 2.5M n-butyllithium in hexane are added. The reaction medium is stirred at −70° C. for 1 hour and 2.79 g of tetrahydrothiopyran-4-one in solution in 30 ml of tetrahydrofuran are added. The reaction medium is stirred at −70° C. for 1 hour and then left at ambient temperature overnight. 50 ml of 2M hydrochloric acid are added and the reaction medium is vigorously stirred for 15 minutes and then extracted with ethyl acetate. The organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel, elution being carried out with a 75/25 mixture of heptane/ethyl acetate.

Workup

  1. stirringThe reaction medium is stirred at −70° C. for 1 hour
  2. waitleft at ambient temperature overnight
  3. stirringthe reaction medium is vigorously stirred for 15 minutes
  4. extractionextracted with ethyl acetate
  5. washwashed with a saturated solution of sodium chloride
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue is chromatographed on silica gel, elution
  9. additionbeing carried out with a 75/25 mixture of heptane/ethyl acetate

Sources & evidence

ORD record
ord-81ba2ea0078846ec9d369199fbe3e890
Source dataset
uspto-grants-2013_02
Patent number
US08372879B2

Reaction notes

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