Hydrochloric Acid → Ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1,4-dienyl)-nona-2,4,6,8-tetraenoate

HRID 439619

반응식

HRID 439619 반응식
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]\[CH:14]=[CH:15]\[C:16](\[CH3:21])=[CH:17]\[C:18]([OH:20])=[O:19].[H][H].[OH-].[K+].Cl.[CH3:28][CH2:29]OC(C)=O.CCCCCC>CO>[CH3:21]/[C:16](/[CH:15]=[CH:14]/[CH:13]=[C:12](/[CH3:22])\[CH:11]=[CH:10]\[C:3]1[C:4]([CH3:8])([CH3:9])[CH:5]=[CH:6][CH2:7][C:2]=1[CH3:1])=[CH:17]\[C:18]([O:20][CH2:28][CH3:29])=[O:19]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 4491719-Cis-Retinoic Acid2회HCID 21226206Ethyl acetate hexaneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10087785Ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1,4-dienyl)-nona-2,4,6,8-tetraenoate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

(XI where R1, R2, R3, R4 and R5 are methyl, R7 is hydrogen) The crude product IX was dissolved in 5 mL of MeOH, followed by addition of 2 mL of 5N aqueous KOH. The reaction was heated to reflux for 30 min., cooled to 0 ° C., and acidified with 1N aqueous HCl. The product was extracted with EtOAc (3×5 mL), and the combined extract was washed with brine, dried over MgSO4 and concentrated. HPLC purification (C18 -ODS, 65% CH3CN-35% H2O-0.5% AcOH) gave 3.2 Curies of pure 3H2 !-9-cis-retinoic acid XI, specific activity >60 Ci/mmol. TLC (20% EtOAc-hexane) Rf 0.26; UV(MeOH) λmax 343 nm; 1H-NMR (CD3OD) δ 1.05 (s, 1-(CH3)2), 1.48 (t, J=3, 9 Hz, 2-CH2), 1.64 (dtt, J=11, 6, 3 Hz, 3-CH2), 1.71 (s, 18-CH3), 1.98 (s, 19-CH3), 2.04 (t, J=6 Hz, 4-CH2), 2.29 (s, 20-CH3), 5.79 (s, 14-CH), 6.11 (d, J=12 Hz, 10-CH), 6.30 (brd, J=16 Hz, 7-CH+12-CH), 6.70 (d, J=17 Hz, 8-CH), 7.11 (dd, J=12 Hz, 16 Hz, 11-CH); 3H-NMR (CD3OD) δ 1.48 (d, J=3 Hz, 2-C3H), 1.64 (d, J=3 Hz, 3-C3H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 30 min.
  3. extractionThe product was extracted with EtOAc (3×5 mL)
  4. extractionthe combined extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customHPLC purification (C18 -ODS, 65% CH3CN-35% H2O-0.5% AcOH)
  9. customgave 3.2 Curies of pure 3H2

출처 및 근거

ORD 기록
ord-02a6d9079dc84d4fa5b839258680b6af
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514821

연결된 노트

불러오는 중…