Sodium hydride → HCID 58381710, compound

HRID 410056Notes

Reaction equation

HRID 410056 reaction equation
[CH2:1]([SH:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20].[H-].[Na+].Br[C:25]([CH3:33])([CH2:31]C)[C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[CH2:1]([S:21][C:25]([CH3:33])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 220969ethyl 2-bromo-2-methylbutanoateHCID 58381715HCID 58381715, compound

Product 1

HCID 58381710HCID 58381710, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaene-1-thiol (305 mg, 1.00 mmol) in dry DMF (10 mL) at 0° C. under inert atmosphere was added NaH (60% in mineral oil, 44 mg, 1.1 mmol). After fifteen minutes ethyl 2-bromo-2-methylbutyrate (154 μL, 1.05 mmol) was added and the mixture was stirred for 1.5 hour at 0° C. The reaction mixture was quenched by addition of sat. aq. NH4Cl (20 mL). Water (20 mL) and heptane (50 mL) were added and the phases were separated. The water phase was extracted with heptane (2×25 mL). The combined organics were washed with water (25 mL) and brine (2×25 mL), dried (MgSO4), filtered and evaporated to give 377 mg of the title compound as a crude oil. Purification by flash chromatography on silica gel using isocratic elution (heptane:EtOAc 98:2) afforded 307 mg (77% yield) of the title compound as oil.

Workup

  1. customThe reaction mixture was quenched by addition of sat. aq. NH4Cl (20 mL)
  2. additionWater (20 mL) and heptane (50 mL) were added
  3. customthe phases were separated
  4. extractionThe water phase was extracted with heptane (2×25 mL)
  5. washThe combined organics were washed with water (25 mL) and brine (2×25 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-0b0d95d87e664f7f92802796bddeb11d
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

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