Water → HCID 20364800, compound

HRID 1678921Notes

Reaction equation

HRID 1678921 reaction equation
C([Li])CCC.[CH:6]([NH:9]C(C)C)(C)C.C(CC[C:20]([O:41]CC)([O:38][CH2:39][CH3:40])[CH2:21][S:22][CH2:23][C:24]([O:35][CH2:36][CH3:37])([O:32][CH2:33][CH3:34])CCC(OCC)=O)(OCC)=O.O.[CH3:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>O1CCCC1>[CH2:36]([O:35][CH:24]([O:32][CH2:33][CH3:34])[CH2:23][S:22][CH:21]([CH2:45][C:46]#[C:47][CH2:48][CH2:49][CH2:50][C:6]#[N:9])[C:20]([O:38][CH2:39][CH3:40])=[O:41])[CH3:37]

Participants

7

Reactant 5

HCID 962WaterHCID 7912DiisopropylamineHCID 8058HexaneHCID 88809012HCID 88809012, compoundHCID 178418339Butyllithium

Product 1

HCID 20364800HCID 20364800, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The starting material is prepared as follows: To the solution, made by adding dropwise 132 ml of n-butyl lithium in hexane to 21.2 g of diisopropylamine in 500 ml of tetrahydrofuran while stirring under nitrogen at -30° for 15 minutes, and cooling it to -70°, 49.5 g of carboethoxyethyl-2,2-diethoxy ethylsulfide are added dropwise over a period of 4 minutes. After stirring at -70° for 1 hour, 49.2 g of 7-iodo-5 -heptynoic acid nitrile are added dropwise during 10 minutes. The mixture is stirred at -70° for 6 hours and allowed to warm up to room temperature overnight. It is poured into water, extracted with diethyl ether, the extract washed with water, dried and evaporated, to yield the ethyl 2-(2,2-diethoxyethylmercapto)-8 cyano-4-octynoate.

Workup

  1. customThe starting material is prepared
  2. temperaturecooling it to -70°
  3. stirringAfter stirring at -70° for 1 hour
  4. stirringThe mixture is stirred at -70° for 6 hours
  5. extractionextracted with diethyl ether
  6. washthe extract washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-ae8d6efb2e9f4195a6910592071ac132
Source dataset
uspto-grants-1978_03
Patent number
US04077980

Reaction notes

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