Piperidine → 6-Pentyl-6-methyl-2-oxo-1,4-oxathiane-3-acetic acid

HRID 1703810Notes

Reaction equation

HRID 1703810 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH:5]([C:16]([OH:18])=[O:17])[S:6][CH2:7][C:8](O)([CH3:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].O=S(Cl)Cl.N1CCCCC1>C(Cl)(Cl)Cl>[CH2:9]([C:8]1([CH3:14])[O:17][C:16](=[O:18])[CH:5]([CH2:4][C:3]([OH:2])=[O:19])[S:6][CH2:7]1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 544848136-Hydroxy-3-hydroxycarbonyl-6-methyl-4-thiaundecanoic acid methyl ester

Product 1

HCID 227607726-Pentyl-6-methyl-2-oxo-1,4-oxathiane-3-acetic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.7 g of 6-hydroxy-3-hydroxycarbonyl-6-methyl-4-thiaundecanoic acid methyl ester and 1.25 g of SOCl2 are stirred for 2 hours in 40 ml of chloroform at room temperature. The mixture is boiled briefly. After cooling, 0.5 ml of piperidine, dissolved in 20 ml of chloroform is added thereto. The resultant mixture is further stirred for 1 hour at 30°. After the usual working up, 6-pentyl-6-methyl-2-oxo-1,4-oxathiane-3-acetic acid is obtained.

Workup

  1. temperatureAfter cooling
  2. additionis added

Sources & evidence

ORD record
ord-1ebe0ee7dd4b4508baebe09bfa0e7f6c
Source dataset
uspto-grants-1978_11
Patent number
US04125622

Reaction notes

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