Sodium Chloride → HCID 86670079, compound

HRID 405008Notes

Reaction equation

HRID 405008 reaction equation
[Na+].[Cl-].[CH2:3]([C:10](=[C:13]=[CH2:14])[CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCCl.CCOCC>[CH2:3]([C:10](=[C:13]=[CH2:14])[CH:11]=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 11788457β-Ethenylidenebenzenepropanol

Product 1

HCID 86670079HCID 86670079, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Fe(NO3)3.9H2O (20.3 mg, 0.05 mmol), 1,2-dichloroethane (DCE, 4 mL), 2,2,6,6-tetramethylpiperidinyloxy (TEMPO, 15.6 mg, 0.10 mmol) and NaCl (5.8 mg, 0.10 mmol) were added to a 10 mL-three-necked flask and were stirred for 5 mins at room temperature under oxygen atmosphere. 2-benzylbuta-2,3-dienol (160.6 mg, 1.0 mmol) was dissolved in DCE (1 mL) and then added to the reaction solution dropwise, and the reaction was monitored by TLC till it was complete. Then the reaction solution was diluted with ether (30 mL), dried over anhydrous MgSO4, filtered by a short pad of silica gel, and then concentrated to yield the crude products. Further purification by column chromatography on silica gel (petroleum ether:ethyl acetate=20:1) afforded the target product 2-benzylbuta-2,3-dienal (114.5 mg, 72%). 1H NMR (300 MHz, CDCl3) δ 9.61 (s, 1H), 7.31-7.15 (m, 5H), 5.28 (t, J=2.4 Hz, 2H), 3.52 (t, J=2.6 Hz, 2H); 13C NMR (75.4 MHz, CDCl3) δ 222.50, 191.41, 138.52, 128.84, 128.35, 126.41, 110.62, 80.83, 30.84; IR (neat) 2827, 2728, 1955, 1928, 1677, 1602, 1495, 1454, 1426, 1227, 1144, 1071, 1030 cm−1; MS (EI) m/z 158 (M+, 5.25), 129 (100); HRMS: calcd. for C11H10O (M+): 158.0732. found: 158.07333.

Workup

  1. additionadded to the reaction solution dropwise
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered by a short pad of silica gel
  4. concentrationconcentrated
  5. customto yield the crude products
  6. customFurther purification by column chromatography on silica gel (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-f7402025b5634670b74231268d9aeb2c
Source dataset
uspto-grants-2014_06
Patent number
US08748669B2

Reaction notes

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