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

HRID 985494

반응식

HRID 985494 반응식
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]

참가 물질

5

반응물 3

HCID 5055AcetylresorcinolHCID 139400Triisopropylsilyl chlorideHCID 2733832Lithium Hexamethyldisilazide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-05f88b98537b45a9a32b7f014cc764ab
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872730B2

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