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

HRID 493455노트

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HRID 493455 반응식
[CH2:1]([Si]1(OC(C)C)N(C)[C@@H](C)[C@H](C2C=CC=CC=2)O1)[CH:2]=[CH2:3].[CH:21](=[O:30])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[C:24]1([CH2:23][CH2:22][C@@H:21]([OH:30])[CH2:3][CH:2]=[CH2:1])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 8857Ethyl AcetateHCID 57681756(4S,5S)-2-Allyl-2-isopropoxy-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine

생성물 1

HCID 10313346(3R)-1-phenyl-hex-5-en-3-ol수율 69%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
21 °C

실험 절차

Enantioselective allylation of dihydrocinnamaldehyde to give (3R)-1-phenyl-hex-5-en-3-ol: To a solution of (4S,5S)-2-Allyl-2-isopropoxy-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (0.437 g, 1.5 mmol) in toluene (2.5 mL) was added dihydrocinnamaldehyde (0.132 mL, 1.0 mmol). The mixture was allowed to stir at ambient temperature (˜21° C.) for 18 hours. To this solution was added 1N HCl (4 mL) and EtOAc (4 mL) and the mixture was stirred for 10 min. The layers were separated and the aqueous layer was extracted with EtOAc (3×5 mL). The combined organics were dried over MgSO4, filtered, and concentrated. The residue was purified by chromatography on silica gel (5% EtOAc/hexanes) to afford 0.119 g (69%) of (3R)-1-phenyl-hex-5-en-3-ol in 94% enantiomeric excess (ee).

후처리

  1. stirringthe mixture was stirred for 10 min
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3×5 mL)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-4b8f7ea544b440cab756c1c6bb4725d2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534905B2

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