Ethyl vinyl ether → HCID 59557744, compound

HRID 2403768Notes

Reaction equation

HRID 2403768 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]([OH:16])[CH3:15])=[CH:10][CH:9]=1.[CH:21]([O:23][CH2:24][CH3:25])=[CH2:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH:14]([O:16][CH:21]([O:23][CH2:24][CH3:25])[CH3:22])[CH3:15])=[CH:17][CH:18]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 59557778HCID 59557778, compound

Product 1

HCID 59557744HCID 59557744, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(5-bromo-2-chlorobenzyl)phenoxy)propan-2-ol (857 mg, 2.4 mmol) in dichloromethane (20 mL) was added ethyl vinyl ether (1.2 mL, 12 mmol) and pyridinium p-toluenesulfonate (24 mg), and the mixture was stirred at room temperature for 2 h, whereupon starting material had been completely consumed as determined by TLC (eluent PE:EA=1:1). Solid sodium bicarbonate (5 g) was added, and the mixture was stirred for 10 min. Water (25 mL) was added, and the mixture was extracted with ethyl acetate, washed with sodium chloride, and dried over sodium sulfate. The residue was concentrated and purified by column chromatography to obtain intermediate CZ (900 mg, yield 87%) as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ 7.23-7.30 (m, 3H), 7.09-7.11 (m, 2H), 6.85-6.87 (m, 2H), 4.86-4.94 (m, 1H), 4.10-4.13 (m, 1H), 4.00 (s, 2H), 3.84-3.99 (m, 1H), 3.69-3.72 (m, 1H), 3.50-3.59 (m, 1H), 1.19-1.37 (m, 9H).

Workup

  1. customhad been completely consumed
  2. additionSolid sodium bicarbonate (5 g) was added
  3. stirringthe mixture was stirred for 10 min
  4. additionWater (25 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed with sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationThe residue was concentrated
  9. custompurified by column chromatography
  10. customto obtain intermediate CZ (900 mg, yield 87%) as a yellow oil

Sources & evidence

ORD record
ord-ade2e26d67044690b0b4ca9b498b88ed
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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