Ethanol → HCID 71268230, compound

HRID 1519678Notes

Reaction equation

HRID 1519678 reaction equation
[OH-].[Na+].C(O)C.O.[O:7]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:9][CH2:8]1>C1COCC1.C(O)(=O)C>[O:7]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)=[CH:19][CH:20]=2)[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 71268277HCID 71268277, compound

Product 1

HCID 71268230HCID 71268230, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 10% aqueous solution (6.6 mL) of sodium hydroxide was added to a solution, in THF (15 mL), ethanol (15 mL) and water (10 mL), of ethyl 4-{[4-(1,4-oxazepan-4-ylmethyl)phenyl]ethynyl}benzoate (1.5 g) as obtained in Example 5-(2). The mixture was stirred for 3 hours at room temperature, and then the reaction mixture was neutralized with acetic acid (5.0 mL). The reaction mixture was concentrated, and water was added. The precipitated solid was filtered off and dried to obtain 4-{[4-(1,4-oxazepan-4-ylmethyl)phenyl]ethynyl}benzoic acid (white solid) (0.92 g, 67%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. filtrationThe precipitated solid was filtered off
  4. customdried

Sources & evidence

ORD record
ord-5ea4a0298c95403b9ebda013044f85dd
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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