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

HRID 2757

反応式

HRID 2757 の反応式
[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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
-15 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2272a341dfe943cb9a6785a30ad21c5c
出典データセット
uspto-grants-1998_03
特許番号
US05731315

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