Tetrahydrofuran → HCID 54518750, compound

HRID 597432Notes

Reaction equation

HRID 597432 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O1CCCC1.[Na].[CH2:24]([O:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30]Br)[CH3:25]>C(O)C>[CH2:24]([O:26][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][S:17][C:14]1[CH:13]=[CH:12][C:11]([C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[CH:16][CH:15]=1)[CH3:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 76300Ethyl 4-bromobutyrateHCID 5360545SodiumHCID 9859657HCID 9859657, compound

Product 1

HCID 54518750HCID 54518750, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 5 g of the crude 4-(1-adamantyl)-thiophenol obtained above, in 25 ml of absolute ethanol and 25 ml of absolute tetrahydrofurane is added dropwise to a solution of 500 mg of sodium in 20 ml of absolute ethanol whilst stirring in a dry nitrogen atmosphere, and 2.9 ml of 4-bromobutyric acid ethyl ester are then added under the same conditions. After completion of the addition, the mixture is heated to 50° C for 14 hours. It is then evaporated to dryness in vacuo and the evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 100 ml of 2 N hydrochloric acid. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Chromatography of the evaporation residue on 240 g of silica gel, with benzene as the eluant, yields chromatographically pure 4-[4-(1-adamantyl)-phenylthio]-butyric acid ethyl ester in the form of a yellow-brown oil (IR spectrum: C=O band at 1,740 cm1- (in CH2Cl 2)).

Workup

  1. additionare then added under the same conditions
  2. additionAfter completion of the addition
  3. customIt is then evaporated to dryness in vacuo
  4. customthe evaporation residue is partitioned between 3 times 100 ml of methylene chloride and 100 ml of 2 N hydrochloric acid
  5. washThe organic phases are washed until neutral,
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f630845a7db4cb89c112a60b92497f4
Source dataset
uspto-grants-1977_03
Patent number
US04013719

Reaction notes

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