Pentane → HCID 22568974、化合物

HRID 24194ノート

反応式

HRID 24194 の反応式
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9])=[CH:4][C:3]=1[C:19]([CH3:22])([CH3:21])[CH3:20].C([Li])(C)(C)C.CCCCC.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>CCOCC>[C:19]([C:3]1[CH:4]=[C:5]([O:6][Si:7]([CH:14]([CH3:16])[CH3:15])([CH:11]([CH3:12])[CH3:13])[CH:8]([CH3:9])[CH3:10])[CH:17]=[CH:18][C:2]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])([CH3:22])([CH3:20])[CH3:21]

参加物

6

反応物 4

HCID 8003PentaneHCID 10928Ethyl chloroformateHCID 22568937HCID 22568937、化合物2 回HCID 178418306HCID 178418306、化合物

生成物 1

HCID 22568974HCID 22568974、化合物収率 124.9%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of (4-bromo-3-tert-butyl-phenoxy)-triisopropyi-silane (Intermediate 105, 1.00 g, 2.60 mmols) in 15 mL Et2O cooled to −78° C. was added 3.6 mL of tert-butyllithium, 1.7 M in pentane (395.0 mg, 6.2 mmols). After stirring for 30 minutes ethyl chloroformate (607.6 mg, 5.6 mmols) was added. The resulting solution was warmed to room temperature and quenched by the addition of saturated aqueous NH4Cl. The mixture was extracted with EtOAc and the combined organic layers dried (MgSO4) concentrated under reduced pressure The residue was chromatographed (2-5% EtOAc—hexanes) to give 1.23 g (88%) of the title compound as a colorless oil.

後処理

  1. additionwas added
  2. customquenched by the addition of saturated aqueous NH4Cl
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. concentrationconcentrated under reduced pressure The residue
  6. customwas chromatographed (2-5% EtOAc—hexanes)

出典と根拠

ORDレコード
ord-8e625530a4f24746909f40f9d6e89e53
出典データセット
uspto-grants-2005_02
特許番号
US06855512B2

反応ノート

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