Dimethylformamide → HCID 53857440, compound

HRID 1764563Notes

Reaction equation

HRID 1764563 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[CH:7]=O.[Br-].[CH2:12]([O:14][C:15]([CH:17]=[C:18]([CH3:44])[CH:19]=[CH:20][CH:21]=[C:22]([CH3:43])[CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16])[CH3:13].CN(C)C=O.[Na]>C(O)C>[CH2:12]([O:14][C:15](=[O:16])[CH:17]=[C:18]([CH3:44])[CH:19]=[CH:20][CH:21]=[C:22]([CH3:43])[CH:23]=[CH:7][C:6]1[C:5]([CH3:9])=[C:4]([CH3:10])[S:3][C:2]=1[CH3:1])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27696392,4,5-trimethylthiophene-3-carbaldehydeHCID 5360545SodiumHCID 73674488HCID 73674488, compound

Product 1

HCID 53857440HCID 53857440, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.9 G. of 2,4,5-trimethyl-3-thiophenecarboxaldehyde and 6.75 g. of (7-ethoxycarbonyl-2,6-dimethyl-2,4,6-heptatrienyl)triphenyl phosphonium bromide are dissolved in 50 ml. of dry dimethylformamide. The solution is treated at 10° C. dropwise with a solution of 0.29 g. of sodium in 8 ml. of ethanol. The mixture is subsequently stirred for 4 hours at room temperature, then introduced into 100 ml. of methanol/water 60:40 parts by volume and thoroughly extracted with hexane. The hexane extract is washed with methanol/water (60:40 parts by volume, then with water, dried over sodium sulfate and evaporated. There is obtained 3,7-dimethyl-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoic acid ethyl ester, which melts after recrystallization from hexane at 88°-89° C.

Workup

  1. additionThe solution is treated at 10° C. dropwise with a solution of 0.29 g
  2. additionintroduced into 100 ml
  3. extractionof methanol/water 60:40 parts by volume and thoroughly extracted with hexane
  4. extractionThe hexane extract
  5. washis washed with methanol/water (60:40 parts by volume
  6. dry with materialwith water, dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-28cd4618e0ca4765ba2c249f4fc0fcf1
Source dataset
uspto-grants-1978_09
Patent number
US04116975

Reaction notes

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