Methyl iodide → HCID 178496638, 화합물

HRID 255135

반응식

HRID 255135 반응식
[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

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 24758Sodium hydride2회HCID 178521634HCID 178521634, 화합물

생성물 1

HCID 178496638HCID 178496638, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 then iodomethane (0.49 mL, 7.8 mmol) was added and the mixture was allowed to warm to ambient temperature and stir 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 2×5 mL 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)+.

후처리

  1. stirringstir 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 2×5 mL 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)

출처 및 근거

ORD 기록
ord-c301d87eb73447019140119e24940852
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875639B2

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