Dichloromethane → HCID 16090467, compound

HRID 2381567Notes

Reaction equation

HRID 2381567 reaction equation
C(Cl)Cl.C[O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:29])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[CH:16][CH:15]=1.C[Si](C)(C)[O-].[K+]>C(OCC)(=O)C>[CH3:26][Si:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][O:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([OH:30])=[O:5])=[O:29])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 16090423HCID 16090423, compoundHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 16090467HCID 16090467, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dry DCM (25 mL) was added to 2-[4-(2-trimethylsilanylethoxymethoxy)benzoyl]-benzoic acid methyl ester (3.8 g, 9.8 mmol) followed by potassium trimethylsilanolate (1.53 g, 10.8 mmol). The system was stirred at room temperature under nitrogen for 16 h and monitored by TLC. Removal of the solvent gave a light yellow oil that was taken up into ethyl acetate (100 mL), washed with 5% HCl solution (3×30 mL), brine (30 mL) and dried with MgSO4. The solvent was removed to give 2-[4-(2-trimethylsilanylethoxymethoxy)benzoyl]benzoic acid as a yellow oil (3.66 g, 9.8 mmol, 99%); Rf 0.1 (40:60 EtOAc:petrol). λmax (CH3OH)/nm 276, 217, Abs 1.799, 2.108 respectively. IR: 3215, 3177, 1666, 1593 cm−1. 1H NMR: (300 MHz, CDCl3) δ 0.00 (s, 9H, Si—(CH3)3), 0.96 (m, 2H, R—O—CH2—CH2—Si), 3.76 (m, 2H, O—CH2—CH2—Si), 5.27 (s, 2H, O—CH2—O), 7.04 (m, 2H, Ar—H), 7.34 (m, 1H, Ar—H), 7.52-7.68 (dtd, 2H, J=30.2, 7.6, 1.3 Hz, Ar—H), 7.69 (m, 2H, Ar—H), 8.07 (m, 1H, Ar—H), 10.31 (bs, 1H, COOH). 13C NMR: (75 MHz, CDCl3) δ −3.2, 16.1, 64.8, 90.7, 113.8, 125.7, 126, 127.4, 128.8, 129.1, 129.9, 131.2, 140.9, 159.6, 168.8, 194. LC/MS-ES+ m/z 297.1, 373.1 [MH+]. HRMS (EI) m/z Calcd. for C20H24O5Si: 372.1393. Found 372.1387

Workup

  1. customRemoval of the solvent
  2. customgave a light yellow oil that
  3. washwashed with 5% HCl solution (3×30 mL), brine (30 mL)
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-1124b0ec85b54382bdd66ba569a4f7d6
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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