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Ethyl Acetate → HCID 131734119, 화합물

HRID 1508637
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HRID 1508637 반응식
[H-].[Na+].[CH2:3]([O:10][CH2:11][CH:12]([OH:17])[CH2:13][CH2:14][CH2:15][OH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19].C(OCC)(=O)C>O1CCCC1.O>[CH2:3]([O:10][CH2:11][CH:12]([OH:17])[CH2:13][CH2:14][CH2:15][O:16][Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 13181689HCID 13181689, 화합물

생성물 1

HCID 131734119HCID 131734119, 화합물

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

0.96 g of sodium hydride (60 wt % in oil) was added to a solution of 5.0 g of 5-(benzyloxy)pentane-1,4-diol in 50 mL of tetrahydrofuran in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, 5.3 mL of triisopropylsilyl chloride was added dropwise to the reaction mixture at a temperature of 5° C. to 10° C. The reaction mixture was stirred at room temperature for 1 hour, and it was then added to a mixture of 100 mL of ethyl acetate and 100 mL of water. The organic layer was fractionated. The obtained organic layer was successively washed with 100 mL of a saturated sodium hydrogen carbonate aqueous solution, 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/5 to 1/5), so as to obtain 5.4 g of 1-benzyloxy-5-((triisopropyl)silyloxy)pentan-2-ol in the form of a colorless oily product.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. washThe obtained organic layer was successively washed with 100 mL of a saturated sodium hydrogen carbonate aqueous solution, 100 mL of water and 100 mL of a saturated sodium chloride aqueous solution, and it
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/5 to 1/5)

출처 및 근거

ORD 기록
ord-0c08088f533343c0a1e22beeb3426532
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221865B2

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