Sodium hydride → 3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate

HRID 985478Notes

Reaction equation

HRID 985478 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+].[H][H].[C:16]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1)(=[O:18])[CH3:17]>C1COCC1.C1(C)C=CC=CC=1.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>[C:16]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:21]=1)(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 131017693-Iodophenyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 112210453-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetateYield 52.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triisopropylsilanethiol (2.91 ml, 13.5 mmol) was added dropwise to a suspension of sodium hydride (325 mg, 13.5 mmol) in THF (10 ml). After the evolution of hydrogen ceased, a solution of 3-iodophenyl acetate (2.37 g, 9.0 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.04 g, 0.9 mmol) in toluene (90 ml) was added. After refluxing for 16 h under argon, the reaction was cooled to room temperature and the solvent was evaporated under vacuum. The resulting residue was dissolved in ethyl acetate, washed with 1N NaOH and brine, dried with sodium sulfate, filtered, and evaporated under vacuum. The crude product was chomatrographed over silica gel to yield 1.53 g (52%) of 3-[1,1-bis (Methylethyl)-2-methyl-1-silapropylthio]phenyl acetate. NMR 1H Cl3CD δ: 7.34 (m, 2H), 7.23 (t, 1H, J=2.4 Hz), 6.94 (dd, 1H, J=1.2, 8.4 Hz), 2.28 (s, 3H), 1.25 (m, 3H), 1.08 (d, 18 H, J=7.2 Hz).

Workup

  1. temperatureAfter refluxing for 16 h under argon
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH and brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-ff458401309d4f08a5fd876cd4e86c76
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

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