Hydrochloric Acid → (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol

HRID 530157

반응식

HRID 530157 반응식
[Mg].Br[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:13]([CH:23]([CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]=[O:25])[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O1CCCC1>[CH2:13]([CH:23]([CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]([OH:25])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 10932932(Z)-1-Bromo-4-deceneHCID 89768339HCID 89768339, 화합물

생성물 1

HCID 89775018(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of magnesium turnings (0.6 g, 23.9 mmol) in tetrahydrofuran (5 mL) was slowly added a solution of (Z)-1-bromodec-4-ene 3 (4.5 g, 20.5 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred for 30 minutes at room temperature then a solution of (Z)-2-((Z)-dec-4-enyl)dodec-6-enal 7 in tetrahydrofuran (5 mL) was added. The solution was stirred for 15 minutes at room temperature then poured into 5% hydrochloric acid (50 mL) and ice (100 mL). The solution was extracted with ether (2×150 mL). The combine ether extracts were dried on magnesium sulfate, filtered, and concentrated in vacuo to dryness. The residue was purified by column chromatography (1% ethyl acetate in hexanes) to afford (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol 8 as a colorless oil (4.8 g, 76%). Rf 0.45 (10% EtOAc-Hexanes).

후처리

  1. stirringThe solution was stirred for 15 minutes at room temperature
  2. extractionThe solution was extracted with ether (2×150 mL)
  3. dry with materialThe combine ether extracts were dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography (1% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5fb82f821f6f41ffa5b365403468eadd
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09352042B2

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