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

HRID 985494ノート

反応式

HRID 985494 の反応式
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]

参加物

5

反応物 3

HCID 5055AcetylresorcinolHCID 139400Triisopropylsilyl chlorideHCID 2733832Lithium Hexamethyldisilazide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-05f88b98537b45a9a32b7f014cc764ab
出典データセット
uspto-grants-2005_03
特許番号
US06872730B2

反応ノート

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