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

HRID 493455ノート

反応式

HRID 493455 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
21 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4b8f7ea544b440cab756c1c6bb4725d2
出典データセット
uspto-grants-2009_05
特許番号
US07534905B2

反応ノート

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