Sodium hydride → HCID 66764878, compound

HRID 1466833Notes

Reaction equation

HRID 1466833 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:14]([O:16][C:17](=[O:28])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21](Br)[CH:20]=1)[CH3:15]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([O:16][C:17](=[O:28])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:20]=1)[CH3:15]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

Product 1

HCID 66764878HCID 66764878, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Triisopropylsilanethiol (6.7 mL, 31.2 mmol) was dissolved in THF (75 mL) at 0° C. and sodium hydride (1.25 g, 60% dispersion in mineral oil, 31.3 mmol) was added, then the solution was allowed to warm to room temperature. Meanwhile, (3-bromo-4-methoxy-phenyl)-acetic acid ethyl ester (6.38 g, 23.4 mmol) was dissolved in THF (75 mL) and sparged with N2 (g). The first solution was added to the second and tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was also added. The reaction was heated to reflux overnight then treated to standard aqueous workup. The residue was purified by silica gel chromatography (0-10% EtOAc in hexanes) to give the title compound.

Workup

  1. customsparged with N2 (g)
  2. additionwas also added
  3. temperatureThe reaction was heated
  4. temperatureto reflux overnight
  5. additionthen treated to standard aqueous workup
  6. customThe residue was purified by silica gel chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0bffe1e8d911469b9a0284494fcbb23a
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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