Imidazole → 9-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene

HRID 2252527노트

반응식

HRID 2252527 반응식
[CH3:1][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.N1C=CN=C1.C(N(CC)CC)C.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][C:4]1([CH2:17][O:18][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol

생성물 1

HCID 226391259-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene수율 86.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.16 mmol) was dissolved in 10 ml of N,N-dimethyl formamide, and 0.14 g (2.08 mmol) of imidazole was added thereto. The solution was cooled in ice-water bath to below 5° C., and 0.87 ml of triethyl amine (6.24 mmol) was added thereto. After stirring for 5 minutes, 0.88 g of tert-butyldimethylsilyl chloride (5.82 mmol) in 10 ml of N,N-dimethyl formamide was added drop-wise to the reaction mixture, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with 10 ml of water, and extracted using 30 ml of dichloromethane. The organic phase was wished twice with 20 ml of water, dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.28 g of 9-methoxymethyl-9-[(tert-butyldimethylsilyl )oxymethyl]-fluorene crude product as pale yellow liquid. The crude product was purified by column chromatography using petroleum ether as eluent, to give colorless pure compound.

후처리

  1. stirringthe mixture was stirred for further 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. extractionextracted
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated

출처 및 근거

ORD 기록
ord-4cf6de34f26b4e2fb12f0a95b9820c90
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323431B2

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