Thionyl Chloride → Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.5]decane-7-acetate

HRID 1608272Notes

Reaction equation

HRID 1608272 reaction equation
O[CH2:2][CH:3]1[CH2:7][S:6][C:5]2([CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8]2)[S:4]1.S(Cl)([Cl:21])=O>C1C=CC=CC=1>[Cl:21][CH2:2][CH:3]1[CH2:7][S:6][C:5]2([CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:8]2)[S:4]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19849046Ethyl 2-(hydroxymethyl)-1,4-dithiaspiro[4.5]decane-7-acetate

Product 1

HCID 19849015Ethyl 2-(chloromethyl)-1,4-dithiaspiro[4.5]decane-7-acetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The titled compound was prepared according to the procedure described in Example E using 6.2 g (0.021 mole) of the product of Example D and 2.75 g (0.025 mol) of thionyl chloride in benzene (60 ml). The crude product was chromatographed on silica gel using 5% ethyl acetate/hexane to give two sets of two racemates. The less polar pair of racemates weighed 0.62 g. The more polar pair of racemates weighed 1.3 g.

Workup

  1. customThe crude product was chromatographed on silica gel using 5% ethyl acetate/hexane
  2. customto give two sets of two racemates

Sources & evidence

ORD record
ord-80cf114f8ea349418e13d77ac2f7976f
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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