2-Methyl-2-butene → HCID 67520549, compound

HRID 1925305Notes

Reaction equation

HRID 1925305 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH2:11]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([CH:29]=[O:30])=[CH:24][CH:23]=[C:22]2[N:31]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(=CC)C>C(O)(C)(C)C.S([O-])([O-])=O.[Na+].[Na+]>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([C:29]([OH:6])=[O:30])=[CH:24][CH:23]=[C:22]2[N:31]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86595517HCID 86595517, compound

Product 1

HCID 67520549HCID 67520549, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 24437Sodium SulfiteSolvent

Procedure

A freshly prepared solution of sodium chlorite (16.8 g, 186 mmol) in a 20% aqueous solution of sodium dihydrogen phosphate (155 mL) was added to a solution of 6-(benzyloxy)-4-(dibenzylamino)-1-naphthaldehyde (prepared by the method described in WO 03/014064) (8.50 g, 18.6 mmol) and 2-methyl-2-butene (27.2 g, 41 mL, 387 mmol) in t-butanol (186 mL). The mixture was stirred vigorously at RT for 1 h. The reaction mixture was diluted with a saturated aqueous solution of sodium sulfite (150 mL) and stirred for 15 min. The mixture was concentrated and then partitioned between CH2Cl2 and water. The aqueous phase was separated and extracted with CH2Cl2. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a tan solid. This material was purified via column chromatography on silica gel (eluting with 0-50% EtOAc-hexane) to afford 6-(benzyloxy)-4-(dibenzylamino)-1-naphthoic acid as an orange brown solid. MS (ESI, pos. ion) m/z: 474.1 (M+H). Mass Calc'd for C32H27NO3: 473.

Workup

  1. customprepared by the method
  2. stirringstirred for 15 min
  3. concentrationThe mixture was concentrated
  4. custompartitioned between CH2Cl2 and water
  5. customThe aqueous phase was separated
  6. extractionextracted with CH2Cl2
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a tan solid
  12. customThis material was purified via column chromatography on silica gel (eluting with 0-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-164d1e1d852444338425af40fa188251
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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