Allyl bromide → HCID 58864607、化合物

HRID 1353165ノート

反応式

HRID 1353165 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25].C(OCC)(=O)C>CN(C)C=O.O1CCCC1>[CH2:25]([O:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1)[CH:24]=[CH2:23]

参加物

7

反応物 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11492838methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate

生成物 1

HCID 58864607HCID 58864607、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4.3 g of methyl 2-((1R,3S)-3-hydroxycyclohexyloxymethyl)-6-methylbenzoate are dissolved in 40 ml of dimethylformamide and 1.3 g of sodium hydride (60% strength suspension in paraffin oil) are added. After 40 minutes of stirring, 4 ml of allyl bromide, dissolved in 20 ml of tetrahydrofuran, are added. After 3 hours, 300 ml of ethyl acetate are added and the mixture is washed three times with saturated sodium chloride solution. The combined organic phases are dried over sodium sulfate and the solvents are then removed under reduced pressure. The resulting residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=50:1→5:1. This gives 2.1 g of methyl 2-((1R,3S)-3-allyloxycyclohexyloxymethyl)-6-methylbenzoate as a yellow oil. C19H26O4 (318.42), MS(ESI): 319 (M+H+).

後処理

  1. additionare added
  2. waitAfter 3 hours
  3. washthe mixture is washed three times with saturated sodium chloride solution
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvents are then removed under reduced pressure
  6. customThe resulting residue is purified on silica gel using the mobile phase n-heptane

出典と根拠

ORDレコード
ord-8d4a4262ffb54c49b1adf7b2af30c4d4
出典データセット
uspto-grants-2007_05
特許番号
US07220876B2

反応ノート

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