Methyl iodide → HCID 178496638、化合物

HRID 78517ノート

反応式

HRID 78517 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:13][C@H:12]([OH:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:18]>O1CCCC1>[CH3:18][O:14][C@H:12]1[CH2:13][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11]1

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 24758Sodium hydride2 回HCID 178521634HCID 178521634、化合物

生成物 1

HCID 178496638HCID 178496638、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of cis-3-benzyloxymethylcyclobutanol (Albany Molecular Research Institute, 1.0 g, 5.2 mmol) in 10 mL of tetrahydrofuran at 0° C. was added NaH (0.62 g, 15.6 mmol). The mixture stirred for 15 minutes and iodomethane (0.49 mL, 7.8 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 16 hours. Some starting material remained by TLC so additional NaH (0.21, 5.2 mmol) and iodomethane (0.32 mL, 5.2 mmol) were added and the mixture stirred for an additional 2 hours. The mixture was quenched with 10 mL of NH4Cl and diluted with 10 mL of ethyl acetate. The layers were separated and the aqueous layer was extracted twice with 5 mL portions of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 75% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 207 (M+H)+.

後処理

  1. stirringstirred for 16 hours
  2. additionwere added
  3. stirringthe mixture stirred for an additional 2 hours
  4. customThe mixture was quenched with 10 mL of NH4Cl
  5. additiondiluted with 10 mL of ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted twice with 5 mL portions of ethyl acetate
  8. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification via column chromatography (SiO2, 75% hexanes in ethyl acetate)

出典と根拠

ORDレコード
ord-a4871e9d8c1b44219fbc9f8affc1cd94
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

反応ノート

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