2-Methyl-2-phenyl-1,3-dioxolane → 2-Phenyl-4-penten-2-ol

HRID 1516953

반응식

HRID 1516953 반응식
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6]CCO1.S([O-])(O[CH2:17][CH2:18]CCCCCCCCCC)(=O)=O.[Na+].O.[C:32]1(C)C=CC(S(O)(=O)=O)=CC=1.C([Mg]Br)C=C>O.C(OCC)C>[C:7]1([C:2]([OH:6])([CH2:1][CH:17]=[CH2:18])[CH3:32])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 1380062-Methyl-2-phenyl-1,3-dioxolaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 3423265Sodium Lauryl SulfateHCID 178455850HCID 178455850, 화합물

생성물 1

HCID 1437612-Phenyl-4-penten-2-ol수율 343.4%

시약·촉매·용매 2

HCID 962Water용매2회HCID 3283Diethyl Ether용매2회

반응 조건

온도
25 °C

실험 절차

2-Methyl-2-phenyl-1,3-dioxolane (0.5 g, 3 mmol), sodium dodecyl sulfate (0.2 g, 0.7 mmol) and a stir bar were added to the inside of a PDMS thimble. p-Toluene sulfonic acid monohydrate (0.145 g, 0.8 mmol) dissolved in 4 mL water was added to the inside of the PDMS thimble followed by 2 mL of hexanes. The reaction was stirred at 25° C. for 5 hours. Hexanes (5 mL) and 24 mL of 1 M allyl magnesiumbromide (3.49 g, 24 mmol) in diethyl ether was added to the outside of the PDMS thimble and the reaction was stirred for 14 hours. Water (5 mL) was added. The PDMS thimble was swelled with 20 mL hexanes and 2×20 mL diethyl ether and the organics were combined and dried over MgSO4. The product was purified by flash chromatography eluting with 100% hexanes initially, increasing to 1:49 ethyl acetate:hexanes to yield a colorless oil (0.39 g, 79% yield). 1H NMR (CDCl3): δ 1.54 (s, 3H), 2.09 (s, 1H), 2.49 (dd, J=13.8, 8.4 Hz, 1H), 2.68 (dd, J=13.5, 6.3 Hz, 1H), 5.09-5.16 (m, 2H), 5.55-5.66 (m, 1H), 7.21-7.26 (m, 1H), 7.31-7.36 (m, 2H), 7.41-7.45 (m, 2H). 13C NMR (CDCl3): δ 29.86, 48.42, 73.58, 119.43, 124.72, 126.57, 128.13, 133.63, 147.59.

후처리

  1. stirringthe reaction was stirred for 14 hours
  2. dry with materialdried over MgSO4
  3. customThe product was purified by flash chromatography
  4. washeluting with 100% hexanes initially
  5. temperatureincreasing to 1:49 ethyl acetate

출처 및 근거

ORD 기록
ord-40b9a39f744e4702ab08ebd06fbf8919
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227635B2

연결된 노트

불러오는 중…