Formaldehyde → 11-Dodecen-1-ol

HRID 441134ノート

反応式

HRID 441134 の反応式
[CH2:1](N1C(=O)C2N(C)C=NC=2N(C)C1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12].[Mg].II.C(Br)CCCCCCCCC=C.C=[O:42].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([OH:42])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12]

参加物

8

反応物 6

HCID 712FormaldehydeHCID 807IodineHCID 25517Ammonium ChlorideHCID 28414811-Bromo-1-undeceneHCID 5462224MagnesiumHCID 232958711-(11-Dodecenyl)-3,7-dimethylxanthine

生成物 1

HCID 52072511-Dodecen-1-ol収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

This example illustrates the synthesis of 1-(11-Dodecenyl)-3,7-dimethylxanthine (CT2516). To a suspension of magnesium (6.4 g, 265 mmol) and a crystal of iodine in tetrahydrofuran (40 ml) was added 10-undecenyl bromide (12.25 g, 53.0 mmol) in tetrahydrofuran (30 ml) over 30 min and the reaction stirred for a further 30 min after the addition was complete. The solution was added via a canula over 5 min to a suspension of paraformaldehyde (1.80 g, 60.0 mmol) in tetrahydrofuran (40 ml) and stirred at 25° C. for 16 hr. Saturated ammonium chloride (80 ml) was added and extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (magnesium sulfate) and evaporated to give a residue which was distilled at 2 mm Hg to afford 11-dodecenyl alcohol as a clear liquid (6.53 g, 67%, b.p. 105°-107° C.).

後処理

  1. additionafter the addition
  2. stirringstirred at 25° C. for 16 hr
  3. extractionextracted with diethyl ether (2×100 ml)
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. customevaporated
  6. customto give a residue which
  7. distillationwas distilled at 2 mm Hg

出典と根拠

ORDレコード
ord-5dcd52dba72f4bf09da0d12699644345
出典データセット
uspto-grants-1996_05
特許番号
US05521315

反応ノート

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