Water → HCID 10443476, 화합물

HRID 1721154

반응식

HRID 1721154 반응식
C/C=C(\C1C=CC(O)=CC=1)/C(/C1C=CC(O)=CC=1)=C/C.[CH3:21]/[C:22](/[CH:28]=[CH:29]/[C:30]1[C:35]([CH3:37])([CH3:36])[CH2:34][CH2:33][CH2:32][C:31]=1[CH3:38])=[CH:23]/[C:24](OC)=[O:25].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[CH3:21]/[C:22](/[CH:28]=[CH:29]/[C:30]1[C:35]([CH3:37])([CH3:36])[CH2:34][CH2:33][CH2:32][C:31]=1[CH3:38])=[CH:23]/[CH2:24][OH:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 667476DienestrolHCID 21226445Aluminium lithium hydrideHCID 86749443methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

생성물 1

HCID 10443476HCID 10443476, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

(II, where R1, R2, R3 and R4 are methyl) To 40 mg (0.16 mmol) of methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate I in 2 mL of anhydrous tetrahydrofuran (THF) at -78° C. was added (0.25 mmol) of LiAlH4. The reaction was stirred at -78° C. for 15 min and warmed to room temperature (RT). When the reaction was complete, as monitored by thin-layer chromatography (TLC), 2 mL of H2O was added and the organics extracted with ether and washed 3 X with 5 mL of water. The organic layer was dried with MgSO4, filtered, concentrated in vacuo and the dienol II was used directly in the next step. TLC (20% EtOAc-hexane) Rf 0.26 (cis isomer), 1H-NMR δ1.01 (s, (CH3)2), 1.46 (t, J=6 Hz, CH2 ), 1.62 (dr, J= 6 Hz, J=4 Hz, CH2), 1.70 (s, CH3, 1.91 (s, CH3), 2.01 (t, J=6 Hz, CH2), 4.30 (d, J=6 Hz, CH2 ), 5.54(t,J=6 Hz, CH), 6.19 (d, J=16 Hz, CH), 6.39 (d, J=16 Hz, CH).

후처리

  1. temperaturewarmed to room temperature (RT)
  2. additionwas added
  3. extractionthe organics extracted with ether
  4. washwashed 3 X with 5 mL of water
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b1a2c4d8dfed436a99ab01ac9fa7a994
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508456

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