Diisopropylethylamine → HCID 86698218, compound

HRID 882557Notes

Reaction equation

HRID 882557 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(N(C(C)C)CC)(C)C.[CH2:20]([O:22][CH2:23]OCl)[CH3:21]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:20]([O:22][CH2:23][O:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH3:21]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5227773-MethylsalicylaldehydeHCID 86698219HCID 86698219, compound

Product 1

HCID 86698218HCID 86698218, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-hydroxyl-3-methylbenzaldehyde (1.46 g, 10.7 mol), diisopropyl ethylamine (3.3 mL, 20.0 mmol) and 4-(dimethylamino)pyridine (122 mg, 1.0 mmol) in dichloromethane (35 mL) was added ethoxymethoxyl chloride (1.85 mL, 20.0 mmol) at RT. The mixture was stirred at RT for 17 h. The reaction was quenched with water (30 mL). The product was extracted with CH2Cl2 (3×40 mL). The combined organic extracts were washed with water (50 mL), and brine (50 mL), dried over anhydride Na2SO4. The residue was purified by flash column chromatography (hexanes/ethyl acetate=5:1, v/v) to provide the title compound (2.02 g, 97%) as a colorless oil.

Workup

  1. customThe reaction was quenched with water (30 mL)
  2. extractionThe product was extracted with CH2Cl2 (3×40 mL)
  3. washThe combined organic extracts were washed with water (50 mL), and brine (50 mL)
  4. dry with materialdried over anhydride Na2SO4
  5. customThe residue was purified by flash column chromatography (hexanes/ethyl acetate=5:1

Sources & evidence

ORD record
ord-d79328b9182a40edaf9464b7f9da813c
Source dataset
uspto-grants-2015_03
Patent number
US08993804B2

Reaction notes

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