Formic Acid → HCID 131730102, compound

HRID 2191390Notes

Reaction equation

HRID 2191390 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:42][CH:43]([OH:65])[CH2:44]OC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:22][CH2:23][O:24][Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=[O:67].C([O-])(O)=O.[Na+]>C(OCC)C>[Si:25]([O:24][CH2:23][CH2:22][N:21]([CH:42]([OH:67])[CH:43]([OH:65])[CH3:44])[CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:38]([CH3:41])([CH3:39])[CH3:40])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 516892Sodium BicarbonateHCID 69826455HCID 69826455, compound

Product 1

HCID 131730102HCID 131730102, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Another batch of XIII was prepared using the following procedure: to a solution of VIII (2.0 g, 2.23 mmol) in diethyl ether (3 mL) was added 85% formic acid (8.2 mL) and the resulting reaction mixture was stirred at room temperature. After 20 h, solid NaHCO3 was added portion wise to neutralize the acidic solution. The reaction mixture was then diluted with diethyl ether (80 mL) and sequentially washed with water (25 mL) and saturated aqueous NaCl (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 4% MeOH in CHCl3) furnished XIII (0.97 g, 67%) as oily liquid. NMR spectra coordinates are as follows: 1H NMR (CDCl3): δ 7.70-7.61 (m, 8H), 7.49-7.31 (m, 12H), 3.73-3.55 (m, 6H), 4.397 (dd, J=11.6, 4.4 Hz, 1H), 2.78-2.54 (m, 5H), 2.57 (d, J=6.8 Hz, 1H) 1.02 (s, 18H).

Workup

  1. customAnother batch of XIII was prepared
  2. customthe resulting reaction mixture
  3. washsequentially washed with water (25 mL) and saturated aqueous NaCl (25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification
  8. washby column chromatography (SiO2, elution with 4% MeOH in CHCl3)

Sources & evidence

ORD record
ord-64f454b55ab0454db79a3d0e61dd1a74
Source dataset
uspto-grants-2012_12
Patent number
US08329681B2

Reaction notes

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