Water → HCID 57236704, compound

HRID 375487Notes

Reaction equation

HRID 375487 reaction equation
O.O.O.O.O.O.O.O.O.[S-2:10].[Na+].[Na+].[C:13]1([C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C(OCC)(=O)C>C(O)CCC.ClCCl>[C:13]1([C:19]2([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:20][CH2:21][S:10][CH2:28][CH2:27]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 73972Sodium sulfide nonahydrateHCID 18995294HCID 18995294, compound

Product 1

HCID 57236704HCID 57236704, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

100 g of sodium sulphide nonahydrate are added to a suspension of 140.8 g of 3,3-diphenyl-l,5-bis-(methanesulphonyl-oxy)pentane in 1400 cm3 of 1-butanol. The mixture is refluxed for 2 hours and then cooled to about 20° C. and then 1000 cm3 of water, 500 cm3 of ethyl acetate and 500 cm3 of dichloromethane are added. After stirring, the organic phase is separated, washed successively with 1000 cm3 of water, 500 cm3 of 1N hydrochloric acid, 500 cm3 of a saturated aqueous solution of sodium hydrogen carbonate and 1000 cm3 of water, and then dried over magnesium sulphate and concentrated to dryness at 60° C. under reduced pressure (2.7 kPa). The residue is crystallized from ethyl acetate, the crystals are washed with diisopropyl oxide, drained and dried. 76 g of 4,4-diphenyltetrahydrothiapyran are obtained in the form of white crystals; melting point 134° C.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. customthe organic phase is separated
  3. washwashed successively with 1000 cm3 of water, 500 cm3 of 1N hydrochloric acid, 500 cm3 of a saturated aqueous solution of sodium hydrogen carbonate and 1000 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness at 60° C. under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized from ethyl acetate
  7. washthe crystals are washed with diisopropyl oxide
  8. customdried

Sources & evidence

ORD record
ord-a3cdde5aceb946a1a7cad222a0c4dd64
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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