Water → HCID 59769753, 화합물

HRID 2220357노트

반응식

HRID 2220357 반응식
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([Cl:10])[CH:9]=1.[CH2:12]([C@H:15]1[O:17][C@@H:16]1[CH2:18][OH:19])[CH2:13][CH3:14].O>C1COCC1.[Cl-].[Na+].O.ClCCl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[O:11][C@@H:15]([CH2:12][CH2:13][CH3:14])[C@H:16]([OH:17])[CH2:18][OH:19]

참가 물질

8

반응물 4

HCID 962WaterHCID 115713,5-DichlorophenolHCID 14798Sodium HydroxideHCID 11073386(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)

생성물 1

HCID 59769753HCID 59769753, 화합물수율 26%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
75 °C

실험 절차

Add sodium hydroxide (1N, 9 mL) to a stirred solution of 3,5-dichlorophenol in THF (9 mL) followed by a solution of (R,R)-(3-propyl-oxiranyl)-methanol in THF (5 mL). Heat the reaction mixture at 75° C. overnight, cool to room temperature, add water, brine and dichloromethane, and separate the layers. The aqueous layer is extracted with dichloromethane, the combined organic extracts are washed successively with 1N sodium hydroxide and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Analysis of the crude reaction mixture by 1H NMR reveals a ˜2:1 mixture of the C-3:C-1 adducts. Purification of the crude residue on silica gel eluting with 0-25% EtOAc/hexanes gives the major title compound (332 mg, 26%). 1H NMR (DMSO-d6): 0.86 (dd, 3H, J=4, 4 Hz), 1.21-1.48 (m, 2H), 1.52-1.72 (m, 2H), 3.28-3.45 (m, 2H), 3.60-3.67 (m, 2H), 4.37-4.44 (m, 1H), 4.69 (dd, 1H, J=6, 6 Hz), 4.88 (d, 1H, J=5 Hz), 7.01-7.10 (m, 3H).

후처리

  1. temperaturecool to room temperature
  2. customseparate the layers
  3. extractionThe aqueous layer is extracted with dichloromethane
  4. washthe combined organic extracts are washed successively with 1N sodium hydroxide and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customAnalysis of the crude reaction mixture by 1H NMR
  8. additiona ˜2:1 mixture of the C-3
  9. customPurification of the crude residue on silica gel eluting with 0-25% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-f5c6ff974c5041ab892c980c12cc4f98
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417064B2

반응 노트

불러오는 중…