Hydrochloric Acid → 5-Iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol

HRID 2757

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HRID 2757 반응식
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:18]OCl.[BH4-].[Na+].Cl>C1COCC1.O.CCOCC.CN1CCCN(C)C1=O>[I:12][C:9]1[CH:10]=[CH:11][C:4]([O:3][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:5]([CH:8]=1)[CH2:6][OH:7]

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2526125-IodosalicylaldehydeHCID 4311764Sodium borohydrideHCID 19350948Methoxyethoxylmethoxyl chloride

생성물 1

HCID 537134685-Iodo-2-(2-methoxy-ethoxymethoxy)-benzyl alcohol수율 80.4%

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

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온도
-15 °C

실험 절차

To a solution of sodium hydride (1.2 g of a 60% mineral oil dispersion, 52 mmol) in 25 mL of THF at 0° C., is added 2-hydroxy-5-iodo-benzaldehyde (7.0 g, 28 mmol). To the resulting solution is added 2-methoxy-ethoxymethoxy chloride (3.4 mL, 30 mmol) and 4 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone. The solution is allowed to warm to ambient temperatures. After 45 min., the solution is cooled to -15° C. and 6 mL of a 2M solution of sodium borohydride in THF is added. The solution is stirred for 10 min. After this time, 24 mL of a 2M HCl solution in water is added. The resulting solution is diluted with ether, washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is purified by column chromatography eluting with 40% EtOAc/hexanes to give the title compound (7.6 g, 22.5 mmol) as a white solid.

후처리

  1. temperatureto warm to ambient temperatures
  2. washwashed with water and saturated NaCl
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude material is purified by column chromatography
  7. washeluting with 40% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-2272a341dfe943cb9a6785a30ad21c5c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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