Sulfuryl chloride → HCID 53870149, compound

HRID 326302Notes

Reaction equation

HRID 326302 reaction equation
[O:1]=[C:2]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:11]=2[O:10][C:4]2([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:3]1.S(Cl)([Cl:27])(=O)=O>ClCCl>[Cl:27][C:14]1[C:15]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:11]2[O:10][C:4]3([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]3)[CH2:3][C:2](=[O:1])[C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19736730HCID 19736730, compound

Product 1

HCID 53870149HCID 53870149, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-{(3,4-dihydro-4-oxospiro[2H-1-benzopyran-2,1'-cyclohexan]7-yl)oxy}acetate prepared in Preparation 28) (0.72 g, 2.26 mmol) is dissolved in dry dichloromethane (7.2 ml). To the solution is added dropwise 1M sulfuryl chloride solution in dichloromethane (2.3 ml, 2.3 mmol) at -40° C. with stirring. After 2 hours stirring at -40° to -10° C., the solvent is removed by distillation. The residue is dissolved in dichloromethane, and the solution is washed with water, dried, and concentrated. The residue is applied to a Lober column and eluted with a mixture of ethyl acetate and hexane (1:2). The resulting crude product is recrystallized from a mixture of diethyl ether and hexane to yield the title compound (0.6 g, yield 75%, m.p.=116°-117° C.).

Workup

  1. stirringAfter 2 hours stirring at -40° to -10° C.
  2. customthe solvent is removed by distillation
  3. dissolutionThe residue is dissolved in dichloromethane
  4. washthe solution is washed with water
  5. customdried
  6. concentrationconcentrated
  7. washeluted with a mixture of ethyl acetate and hexane (1:2)
  8. customThe resulting crude product is recrystallized from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-2997d77b6ead46359f8bb8952645fa45
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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