Acetic Anhydride → 5-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

HRID 488234

반응식

HRID 488234 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Mg].[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:18][C:17]=1[CH:25]=[O:26].[C:27](OC(=O)C)(=[O:29])[CH3:28]>O1CCCC1>[CH3:15][C:16]1[O:20][C:19]([Si:21]([CH3:22])([CH3:24])[CH3:23])=[CH:18][C:17]=1[CH:25]([O:26][C:27](=[O:29])[CH3:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 89191-BromododecaneHCID 5462224MagnesiumHCID 157445905Methyl-2-trimethylsilyl-4-furaldehyde

생성물 1

HCID 194331855-Methyl-4-(1-acetoxytridecyl)-2-trimethylsilylfuran

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 1-bromododecane (261 mg, 0.11 mmol) and magnesium turnings (27 mg, 0.11 mmol) in tetrahydrofuran (7 ml) was refluxed under argon for 1 hour. After cooling to room temperature, a solution of 5-methyl-2-trimethylsilyl-4-furaldehyde (158.6 mg, 0.87 mmol) in tetrahydrofuran (1 ml) was added, followed by acetic anhydride (0.25 ml, 2.6 mmol) after 1 hour. Stirring was continued at room temperature overnight and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

후처리

  1. temperaturewas refluxed under argon for 1 hour
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customwas purified by preparative TLC (20×20 cm, 1000 micron silica plate; developed with 5% ethyl ether/hexane)

출처 및 근거

ORD 기록
ord-dca08df96bca4e8999c4587933fcfd3a
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298633

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