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

HRID 493453ノート

反応式

HRID 493453 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aa8b17404072423bbb4374dfb33f22cc
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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