1-Pentene, 5-bromo- → 4-(4-Acetyl-8-hydroxytridec-12-en-1-yl)benzoic acid

HRID 46969

反応式

HRID 46969 の反応式
BrCCCC=C.Cl[CH2:8][CH2:9][CH2:10][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].ClCCCC(O)CCCC=C.ClCCCC(OC(=O)C)CCCC=C.C(OC([CH:50]([C:65](=[O:67])[CH3:66])[CH2:51][CH2:52][CH2:53][C:54]1[CH:64]=[CH:63][C:57]([C:58]([O:60]CC)=[O:59])=[CH:56][CH:55]=1)=O)(C)(C)C.C(C(C(OC(C)(C)C)=O)(CCCC(OC(=O)C)CCCC=C)CCCC1C=CC(C(OCC)=O)=CC=1)(=O)C.C(C(CCCC(OC(=O)C)CCCC=C)CCCC1C=CC(C(OCC)=O)=CC=1)(=O)C>>[C:65]([CH:50]([CH2:8][CH2:9][CH2:10][CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[CH2:51][CH2:52][CH2:53][C:54]1[CH:64]=[CH:63][C:57]([C:58]([OH:60])=[O:59])=[CH:56][CH:55]=1)(=[O:67])[CH3:66]

参加物

8

反応物 7

HCID 707041-Pentene, 5-bromo-HCID 203860321-Chloro-8-nonen-4-olHCID 20386057Ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoateHCID 20386059Ethyl 4-(4-acetyl-8-acetoxytridec-12-en-1-yl)benzoateHCID 203860741-Chloro-4-acetoxy-8-noneneHCID 203860861-Chloro-8-nonen-4-oneHCID 20386088Ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridec-12-en-1-yl)benzoate

生成物 1

HCID 203860714-(4-Acetyl-8-hydroxytridec-12-en-1-yl)benzoic acid

実験手順

The synthesis of this compound is carried out as described in Example 1, except that in Step B(1) an equivalent amount of 5-bromo-1-pentene is used in place of amyl bromide. The product of Step B(1) thus becomes 1-chloro-8-nonen-4-one. Subsequent steps afford in order: Step B(2), 1-chloro-8-nonen-4-ol; Step B(3), 1-chloro-4-acetoxy-8-nonene; Step C, ethyl 4-(4-tert-butoxycarbonyl-5-oxohexyl)benzoate (unchanged from Example 1); Step D, ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridec-12-en-1-yl)benzoate (by substituting 1-chloro-4-acetoxy-8-nonene for 1-chloro-4-acetoxynonane); Step E, ethyl 4-(4-acetyl-8-acetoxytridec-12-en-1-yl)benzoate; and Step F, 4-(4-acetyl-8-hydroxytridec-12-en-1-yl)benzoic acid, obtained as a viscous yellowish oil.

後処理

  1. customThe synthesis of this compound
  2. customSubsequent steps afford in order

出典と根拠

ORDレコード
ord-951cb0e1390b4d569356b790d67f045e
出典データセット
uspto-grants-1979_11
特許番号
US04175203

関連ノート

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