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

HRID 530157

反応式

HRID 530157 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 10932932(Z)-1-Bromo-4-deceneHCID 89768339(Z)-2-((Z)-Dec-4-en-1-yl)dodec-6-enal

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5fb82f821f6f41ffa5b365403468eadd
出典データセット
uspto-grants-2016_05
特許番号
US09352042B2

関連ノート

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