Ethanol → HCID 13656010, compound

HRID 745899Notes

Reaction equation

HRID 745899 reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[CH2:13](O)[CH3:14].N1C=CC=CC=1>O1CCCC1>[CH3:12][Si:2]([CH3:1])([CH3:11])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:13][CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 119900745-Hexynoic acid, 6-(trimethylsilyl)-

Product 1

HCID 13656010HCID 13656010, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.3 gm of 1,1-carbonyldiimidazole in 80 ml of dry tetrahydrofuran under argon, was added a solution of 5.03 gm of 6-trimethylsilyl-5-hexynoic acid in 15 ml of dry tetrahydrofuran. The mixture was stirred for 1 hour. Absolute ethanol (80 ml) and pyridine (1 ml) were then added, and the resulting mixture was stirred at room temperature for 48 hours. The solvent was evaporated and the residual oil was extracted with ether and 1.5% hydrochloric acid. The ethereal layer, which was washed with water and then dried, was evaporated to an oil. This material was purified by distillation, b.p. 70°-75° C. (0.6 mm Hg); IR: 2170, 1735 cm-1.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 48 hours
  2. customThe solvent was evaporated
  3. extractionthe residual oil was extracted with ether and 1.5% hydrochloric acid
  4. washThe ethereal layer, which was washed with water
  5. customdried
  6. customwas evaporated to an oil
  7. distillationThis material was purified by distillation, b.p. 70°-75° C. (0.6 mm Hg)

Sources & evidence

ORD record
ord-83430d2080774b3f8ba143fafc677b13
Source dataset
uspto-grants-1986_07
Patent number
US04602006

Reaction notes

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