Acetylresorcinol → 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate

HRID 985494Notes

Reaction equation

HRID 985494 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)(=[O:13])[CH3:12].[CH:22]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C1COCC1>[C:11]([O:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([O:18][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])[CH:16]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 5055AcetylresorcinolHCID 139400Triisopropylsilyl chlorideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 114610083-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetateYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (73 ml, 73 ml, 1M solution in THF) was added dropwise to a solution of resorcinol monoacetate (10 g, 65.7 mmol) in THF (100 ml) at 78° C. under argon. The solution was stirred for 10 minutes and then triisopropylsilyl chloride (15.5 ml, 73 mmol) was added via syringe. After stirring at room temperature overnight, the mixture was partitioned between water and ethyl acetate. The organic layer was dried, filtered and evaporated under vacuum to yield 13 g of crude 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate which was used in the next step without further purification. NMR 1H Cl3CD δ: 7.19 (t, 1H, J=8 Hz), 6.75 (m, 1H), 6.68 (m, 1H), 6.63 (t, 1H, J=4 Hz), 2.29 (s, 3H), 1.25 (m, 3H), 1.11 (d, 18H, J=7.0 Hz).

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-05f88b98537b45a9a32b7f014cc764ab
Source dataset
uspto-grants-2005_03
Patent number
US06872730B2

Reaction notes

Loading…