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Hydrochloric Acid → 2-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-(1hydroxy-5-phenylpentyl)phenyl)ethyl)propane

HRID 323804
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HRID 323804 반응식
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([NH:16][C:17]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]=[O:45])=[CH:40][CH:39]=1)([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=[O:15])[CH3:14].Cl>O1CCCC1>[C:13]([NH:16][C:17]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH:44]([OH:45])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:40][CH:39]=1)([CH2:27][O:28][Si:29]([C:32]([CH3:33])([CH3:34])[CH3:35])([CH3:31])[CH3:30])[CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])(=[O:15])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 2596681-Bromo-4-phenylbutaneHCID 5462224MagnesiumHCID 155166782-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-formylphenyl)ethyl)propane

생성물 1

HCID 155166792-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-(1hydroxy-5-phenylpentyl)phenyl)ethyl)propane수율 83.2%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of magnesium (0.27 g) in anhydrous tetrahydrofuran (5 ml) was dropwise added a solution of 1-bromo-4-phenylbutane (2.35 g) in anhydrous tetrahydrofuran (5 ml) under a nitrogen atmosphere, and the mixture was stirred for 1.5 hours. To this solution was dropwise added a solution of 2-acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-formylphenyl)ethyl)propane (1.2 g) in anhydrous tetrahydrofuran (15 ml) and the mixture was stirred for 1 hour. 3% Hydrochloric acid was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=2:1) to give the title compound (1.27 g) as a colorless transparent oily substance.

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; hexane: ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-ec9877793fb14af1bd41820b95af093c
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06214873B1

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