Hydrochloric Acid → HCID 58415259, compound

HRID 2075250Notes

Reaction equation

HRID 2075250 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH:22](OC)[O:23]C)=[CH:18][C:17]=3[F:27])=[N:13][C:12]=2[CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.C(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][C:17]=3[F:27])=[N:13][C:12]=2[CH:28]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58415325HCID 58415325, compound

Product 1

HCID 58415259HCID 58415259, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyl-2-(4-(dimethoxymethyl)-2-fluorophenyl)benzo[d]oxazole (0.160 g, 0.424 mmol) was dissolved in 2 mL THF and 1 mL 5N HCl was added. The mixture was stirred for 1 h, diluted with DCM, and quenched with 10N NaOH until basic. The aqueous was extracted 2×DCM. Combined organics were dried over sodium sulfate, filtered, and concentrated to give 4-(5-benzylbenzo[d]oxazol-2-yl)-3-fluorobenzaldehyde as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.09 (s, 1H), 8.43 (t, J=7.3 Hz, 1H), 7.90-8.04 (m, 2H), 7.72-7.83 (m, 2H), 7.38 (d, J=8.5 Hz, 1H), 7.26-7.33 (m, 4H), 7.17-7.24 (m, 1H), 4.11 (s, 2H).

Workup

  1. customquenched with 10N NaOH until basic
  2. extractionThe aqueous was extracted 2×DCM
  3. dry with materialCombined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88504ffde03f47efa0293a3f52952046
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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