N,N-Dimethylaniline → HCID 53784306, compound

HRID 1637105Notes

Reaction equation

HRID 1637105 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:17](Cl)=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.[CH:37]([OH:40])([CH3:39])[CH3:38]>CCOCC>[CH:37]([O:40][C:17](=[O:18])[CH2:16][CH:15]([C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[C:20]#[C:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 3776IsopropanolHCID 54112783HCID 54112783, compound

Product 1

HCID 53784306HCID 53784306, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid chloride (150 mg, 0.42 mmol) and dimethylaniline (100 mg, 0.83 mmol) in Et2O (5 ml) was treated with i-propanol (1 ml) and stirred at 23° for 18 hr. The solvents were evaporated, and the residue taken up in Et2O, washed with 3N HCl, H2O, dried, and the solvent evaporated. The residue was purified by flash chromatography (silica gel, 20% EtOAc/hexane), and gave the titled compound, 82 mg (54%). MP . 1H NMR (400 MHz, CDCl3) δ 7.38 (m, 2 H), 7.30 (m, 3 H), 6.94 (m, 2 H), 6.78 (d, 1 H), 5.02 (m, 1 H), 4.78 (m, 1 H), 4.30 (t, 1 H), 3.80 (s, 3 H), 2.82 (d of d, 1 H), 2.72 (d of d, 1 H), 1.78-1.96 (m, 6 H), 1.60 (m, 2 H), 1.22 (d, 3 H), 1.16 (d, 3 H).

Workup

  1. customThe solvents were evaporated
  2. washwashed with 3N HCl, H2O
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-84f982fb728f4f7083720239eb865e42
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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