Hydrochloric Acid → (3R)-1-phenyl-hex-5-en-3-ol

HRID 493453노트

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HRID 493453 반응식
[CH2:1]([Si]1(Cl)N(C)[C@@H](C)[C@H](C2C=CC=CC=2)O1)[CH:2]=[CH2:3].[CH:18](=[O:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[C:21]1([CH2:20][CH2:19][C@@H:18]([OH:27])[CH2:3][CH:2]=[CH2:1])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 8857Ethyl AcetateHCID 10333223(4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-1-oxa-3-aza-2-silacyclopentane

생성물 1

HCID 10313346(3R)-1-phenyl-hex-5-en-3-ol수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-10 °C

실험 절차

Enantioselective allylation of dihydrocinnamaldehyde to give (3R)-1-phenyl-hex-5-en-3-ol: To a cooled (−10° C.) solution of (4S,5S)-2-Allyl-2-chloro-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (380 mg, 1.5 mmol) in toluene (5 mL) was added dihydrocinnamaldehyde (1.0 mmol). The reaction mixture was maintained at −10° C. for 2 h. To this cooled solution was added 1N HCl (4 mL) and EtOAc (4 mL) and the mixture was vigorously stirred for 15 min. The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The combined organics were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel to give (3R)-1-phenyl-hex-5-en-3-ol in 84% yield and 88% enantiomeric excess (ee).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-aa8b17404072423bbb4374dfb33f22cc
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534905B2

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