Dimethylformamide → HCID 57810562, compound

HRID 1171202Notes

Reaction equation

CN(C)C=O.[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]([OH:22])=[C:18]([CH:21]=1)[CH:19]=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23]([O:26][CH2:27][CH2:28]Br)(=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:27]([O:26][C:23]([C:24]1[O:22][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:21][C:18]=2[CH:19]=1)=[O:25])[CH3:28]

Participants

Conditions

Temperature: 120 °C

Procedure

To a N,N-dimethylformamide (10 mL) solution of 5-benzyloxy-2-hydroxy-benzaldehyde (830 mg, 3.64 mmol) described in Production Example 7-1-2 were added bromoethyl acetate (446 μL, 4.00 mmol) and potassium carbonate (1.01 g, 7.28 mmol) at room temperature, which was stirred at 120° C. for 8 hours. Water was added to the reaction solution at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with water and sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (890 mg, 83%) as a pale yellow oil.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and sat. NaCl
dry with materialby drying over anhydrous magnesium sulfate
filtrationfiltering
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-220458e0904a4265a43035a58675158e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829585B2

Reaction notes

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