Water → HCID 21999530, compound

HRID 1976942Notes

Reaction equation

HRID 1976942 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]Cl.[CH3:8][O:9][C:10]1[C:11]([F:31])=[C:12]([F:30])[C:13]2[C:14](=[O:29])[C:15]3[C:20]([O:21][C:22]=2[C:23]=1[F:24])=[C:19]([F:25])[C:18]([OH:26])=[C:17]([F:27])[C:16]=3[F:28].O>C(Cl)Cl>[CH3:8][O:9][C:10]1[C:11]([F:31])=[C:12]([F:30])[C:13]2[C:14](=[O:29])[C:15]3[C:20]([O:21][C:22]=2[C:23]=1[F:24])=[C:19]([F:25])[C:18]([O:26][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:17]([F:27])[C:16]=3[F:28]

Participants

5

Reactant 3

HCID 962WaterHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 21999561HCID 21999561, compound

Product 1

HCID 21999530HCID 21999530, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxyethoxymethyl chloride (150 mg, 1.2 mmol) is added to a solution of Compound 47 in 10 mL dry CH2Cl2 at 20° C. The reaction mixture is stirred for 1 hour and poured into 50 mL water. The product is extracted with diethyl ether (30 mL×2) and ethyl acetate (30 mL). The combined organic extracts are washed with 5% citric acid solution (50 mL), and brine (30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to yield 425 mg yellow oil. The crude oil is then recrystallized from isopropyl alcohol to yield 240 mg (51%) of Compound 48 as a colorless solid. 1H-NMR (d6-DMSO) 5.48 (s, 2H); 4.36 (s, 3H); 3.99 (t, J=Hz, 2H); 3.58 (t, J=Hz, 2H); 3.36 (s, 3H). 19F-NMR (d6-DMSO) 142.90 (d, J=12.7, 1F); 142.97 (d, J=12.4 Hz, 1F); 153.12 (d, J=13.5 Hz, 1F); 155.54 (d, J=19.7 Hz, 1F); 155.82 (d, J=11.3 Hz, 1F); 157.13 (d, J=19.5 Hz, 1F).

Workup

  1. extractionThe product is extracted with diethyl ether (30 mL×2) and ethyl acetate (30 mL)
  2. washThe combined organic extracts are washed with 5% citric acid solution (50 mL), and brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe75c4da16894e5cb25f8c2d50fb894c
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

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