Water → (E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethyloct-6-en-3-ol

HRID 49323ノート

反応式

HRID 49323 の反応式
[CH2:1]([C:3]([OH:32])([CH2:30][CH3:31])[CH2:4][CH2:5]/[CH:6]=[C:7](/[C:9]1[S:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([C:26](OC)=[O:27])[C:19](=[CH:24][CH:25]=2)[C:20](OC)=[O:21])=[CH:11][CH:10]=1)\[CH3:8])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[OH:27][CH2:26][C:18]1[CH:17]=[C:16]([CH:25]=[CH:24][C:19]=1[CH2:20][OH:21])[O:15][CH2:14][C:12]1[S:13][C:9](/[C:7](/[CH3:8])=[CH:6]/[CH2:5][CH2:4][C:3]([CH2:30][CH3:31])([OH:32])[CH2:1][CH3:2])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 962WaterHCID 15516125dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 10111871(E)-7-[5-(3,4-bis-Hydroxymethyl-phenoxymethyl)-2-thienyl]-3-ethyloct-6-en-3-ol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

350 mg (0.76 mmol) of dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalate are dissolved in 20 mL of anhydrous ethyl ether. 70 mg (1.8 mmol) of lithium aluminium hydride are added and the reaction medium is stirred at room temperature for 30 minutes. 400 mL of water are then added slowly and the medium is filtered. The filtrate is concentrated under reduced pressure and the residue obtained is then purified by chromatography on a column of silica (eluent: 70 ethyl acetate/30 heptane). A white solid (m.p.: 100-102° C.) is obtained (m=175 mg; Y=58%).

後処理

  1. filtrationthe medium is filtered
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue obtained
  4. customis then purified by chromatography on a column of silica (eluent: 70 ethyl acetate/30 heptane)

出典と根拠

ORDレコード
ord-ff66c071e48c4708934910615263cea6
出典データセット
uspto-grants-2004_03
特許番号
US06706725B1

反応ノート

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