Hydrochloric Acid → HCID 9888784, 화합물

HRID 988007노트

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HRID 988007 반응식
[O:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=[O:13])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[N+:25]([CH3:28])([O-:27])=[O:26].Cl>C1COCC1>[O:1]([C:9]1[CH:10]=[C:11]([C@@H:12]([OH:13])[CH2:28][N+:25]([O-:27])=[O:26])[CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 109374483,4-di(t-butyldimethylsiloxy)benzaldehyde

생성물 1

HCID 9888784HCID 9888784, 화합물수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

100 mg (0.26 mmol) of 3,4-di(t-butyldimethylsiloxy)benzaldehyde was dissolved in 10 ml of THF under the atmosphere of argon at −40° C., and 0.30 ml of rare earth metal complex solution A1 was mixed into the solution. After stirring for 30 minutes, 79.3 mg (1.3 mmol) of nitromethane was added dropwise to the mixture. After 67-hour reaction time, 2 ml of 1 N aqueous solution of hydrochloric acid was added to stop the reaction. Then, after 50 ml of ethyl accetate was added, the mixture was subjected to oil-water separation twice with 20 ml of saturated salt solution and once with 20 ml of water, and the ethyl accetate layer was dehydrated with sodium sulfate anhydride and concentrated within evaporator, followed by the purification of the concentrate by silica gel chromatography (n-hexane/acetone=10/1), after which (R)-1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-nitroethanol with an optical purity of 92% e.e. was obtained in a yield of 93%.

후처리

  1. additionwas added
  2. customthe reaction
  3. additionThen, after 50 ml of ethyl accetate was added
  4. customthe mixture was subjected to oil-water separation twice with 20 ml of saturated salt solution and once with 20 ml of water
  5. concentrationconcentrated within evaporator
  6. customfollowed by the purification of the
  7. concentrationconcentrate by silica gel chromatography (n-hexane/acetone=10/1)

출처 및 근거

ORD 기록
ord-6022e130a1ab4e5099de857435bf0c9e
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632955B1

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