3-Methoxybenzaldehyde → HCID 86751161, compound

HRID 2258029Notes

Reaction equation

HRID 2258029 reaction equation
CCCCCCC=CCCC.[C:12]([O:16][C:17]([NH:19][CH:20](P(OC)(OC)=O)[C:21]([O:23][CH3:24])=[O:22])=[O:18])([CH3:15])([CH3:14])[CH3:13].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=O>C(Cl)Cl>[C:12]([O:16][C:17]([NH:19][C:20](=[CH:36][C:35]1[CH:38]=[CH:39][CH:40]=[C:33]([O:32][CH3:31])[CH:34]=1)[C:21]([O:23][CH3:24])=[O:22])=[O:18])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 115693-MethoxybenzaldehydeHCID 136496Undec-4-eneHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

Product 1

HCID 86751161HCID 86751161, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.70 mL (4.7 mmol) of 1,8-diazabicyclo[5.4.0.]undec-7-ene (DBU) and 1.40 g (4.7 MMOL) of tert-butoxycarbonylamino-(dimethoxyphosphoryl)acetic acid, methyl ester of Example 29 in 14 mL of methylene chloride is stirred at room temperature for 25 minutes. A quantity of 0.64 g (4.7 mmol) of 3-methoxybenzaldehyde is added and the solution is stirred at room temperature overnight. Methylene chloride (100 mL) is added and the solution is washed with 80mL of 1N hydrochloric acid and then with 80 mL of brine. The dried (magnesium sulfate) organic phase is evaporated and the product is purified by silica gel chromatography, eluting with 18% ethyl acetate to give pure product as a white powder; wt 1.25 g (86%);

Workup

  1. washthe solution is washed with 80mL of 1N hydrochloric acid
  2. dry with materialThe dried (magnesium sulfate) organic phase
  3. customis evaporated
  4. customthe product is purified by silica gel chromatography
  5. washeluting with 18% ethyl acetate
  6. customto give pure product as a white powder

Sources & evidence

ORD record
ord-0a3ec4ddb55a45b1831e0c499456f1fe
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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