Hydrochloric Acid → HCID 18469814, compound

HRID 2228419Notes

Reaction equation

HRID 2228419 reaction equation
O[CH2:2][C:3]1([CH2:8][O:9][CH3:10])[CH2:7][S:6][S:5][CH2:4]1.[H-].[Na+].S1([O:19][CH2:18][CH2:17][O:16]1)(=O)=O.Cl>C1COCC1>[OH:16][CH2:17][CH2:18][O:19][CH2:2][C:3]1([CH2:8][O:9][CH3:10])[CH2:7][S:6][S:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 140751,3,2-Dioxathiolane, 2,2-dioxideHCID 24758Sodium hydrideHCID 18469812HCID 18469812, compound

Product 1

HCID 18469814HCID 18469814, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-Hydroxymethyl-4-methoxymethyl-1,2-dithiacyclopentane (0.1 g) in THF (20 ml) was added to a suspension of sodium hydride (0.03 g) in THF (20 ml) and the mixture was stirred at room temperature for 30 min. Ethylene sulfate (0.14 g) was added and the resulting mixture stirred at room temperature for 48 h. Hydrochloric acid (3M, 5 ml) was added, and the aqueous layer extracted with ethyl acetate (5×20 ml). The organic layers were combined and washed with water (50 ml) and dried (Na2SO4). The solvent was removed under reduced pressure and the resulting oil purified by flash chromatography (ethyl acetate-light petroleum, 1:1 as eluant) to give 4-(2-hydroxyethoxy)methyl-4-methoxymethyl-1,2-dithiacyclopentane (66.8 mg, 54%). 1H-n.m.r. (CDCl3) δ2.93 (AB quartet, 4H), 3.34 (s, 3H), 3.36 (s, 2H), 3.46 (s, 2H), 3.56 (m, 2H). 3.70 (m, 2H); 13C-n.m.r. (CDCl3) δ44.7, 56.2, 59.3, 61.6, 72.2, 72.3, 74.2; m/z 224 (M+)

Workup

  1. stirringthe resulting mixture stirred at room temperature for 48 h
  2. extractionthe aqueous layer extracted with ethyl acetate (5×20 ml)
  3. washwashed with water (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting oil purified by flash chromatography (ethyl acetate-light petroleum, 1:1 as eluant)

Sources & evidence

ORD record
ord-a24b0c3a79e94cbf96f10e9773807cd8
Source dataset
uspto-grants-2002_07
Patent number
US06417009B1

Reaction notes

Loading…