Thionyl Chloride → HCID 13884687, compound

HRID 979689Notes

Reaction equation

HRID 979689 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:18]([CH3:20])[CH3:19])[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])=[O:12])=[CH:6][CH:5]=1)[CH3:2].S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl.C(OCC)(=O)C.CCCCCC>[Cl:23][C:5]1[CH:6]=[C:7]([CH:10]([CH:18]([CH3:19])[CH3:20])[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])=[O:12])[CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 13884686HCID 13884686, compound

Product 1

HCID 13884687HCID 13884687, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of 0.15 g (0.55 mM) of Compound No. 2 (2-butynyl 2-(4-ethoxyphenyl)isovalerate) in 5 ml of chloroform, 0.76 g (5.5 mM) of thionyl chloride was added, and the mixture was stirred for 16 hours at room temperature. After condensing the reaction mixture, the condensate was subjected to silica gel column chromatography while using a 1:30 mixture of ethyl acetate and n-hexane as an eluent, thereby 0.14 g of the colourless and only compound No. 24 was obtained (yield: 80%).

Workup

  1. customAfter condensing the reaction mixture
  2. custom24 was obtained (yield: 80%)

Sources & evidence

ORD record
ord-f7eb36821d0644f6963f02800378a548
Source dataset
uspto-grants-1987_05
Patent number
US04668815

Reaction notes

Loading…