Dimethylformamide → Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

HRID 1609347Notes

Reaction equation

HRID 1609347 reaction equation
O[CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cl-].[Li+].CN(C)C=O.CS([Cl:37])(=O)=O>CCCCCC.C(OCC)(=O)C.CCOCC.O>[Cl:37][CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:22])[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 54363154Ethyl 14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

Product 1

HCID 54546229Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoateYield 88%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of ethyl 14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate (71.0 mg, 0.20 mmol), τ-collidine (26.7 mg, 0.22 mmol), lithium chloride (8.5 mg, 0.20 mmol), and dimethylformamide (1 ml) was added with stirring methanesulfonyl chloride (25.2 mg, 0.22 mmol) on an ice-water bath and under nitrogen atmosphere. The stirring was continued at the same temperature for 5 hours. After confirmation of disappearance of the starting material, water and ether were added to the reaction mixture. The organic layer was separated, washed with water, dried over MgSO4, and condensed to give a residue, which was then subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate (10:1)). Relevant fractions gave the aimed ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate (64.6 mg, 86% ). ##STR46##

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over MgSO4, and condensed
  4. customto give a residue, which

Sources & evidence

ORD record
ord-28dd66159d954a1d85c4994a22d0c21b
Source dataset
uspto-grants-1995_03
Patent number
US05399724

Reaction notes

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