Water → HCID 53850289, compound

HRID 2231184Notes

Reaction equation

HRID 2231184 reaction equation
C([N:9]1[C:22]2[CH:21]=[CH:20][C:19]([NH:23][CH2:24][CH3:25])=[CH:18][C:17]=2[O:16][C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([NH:26][CH2:27][CH3:28])[CH:14]=2)(=O)C1C=CC=CC=1.C([BH-](CC)CC)C.[Li+].[OH:37][C:38]1[C:46]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][C:39]=1[C:51]([CH3:54])([CH3:53])[CH3:52].O>O1CCCC1>[C:51]([C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:38]=1[OH:37])[C:42]([N:9]1[C:22]2[CH:21]=[CH:20][C:19]([NH:23][CH2:24][CH3:25])=[CH:18][C:17]=2[O:16][C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([NH:26][CH2:27][CH3:28])[CH:14]=2)=[O:43])([CH3:54])([CH3:53])[CH3:52]

Participants

6

Reactant 4

HCID 962WaterHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 23664628LithiumtriethylborohydrideHCID 53960725HCID 53960725, compound

Product 1

HCID 53850289HCID 53850289, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution containing 4.29 g of 10-benzoyl-3,7-diethylaminophenoxazine in 15 ml of tetrahydrofuran was added to 26 ml of 1M lithium triethylborohydride in tetrahydrofuran. After the addition was complete, the mixture was stirred for one hour. To this was added, over 15 minutes, 3.1 grams of 4-hydroxy-3,5-di-t-butylbenzoyl chloride. The mixture was stirred for one hour. Water was added and the product extracted into ethyl acetate. The solvent was removed and the product filtered through a pad of silica gel, and eluted with 1:3 ethyl acetate-hexane. Additional chromatography over alumina and elution with 1:4 ethyl acetate-hexane followed by recrystallization from etherhexane and finally from methanol gave 0.6 gm of the color forming developer.

Workup

  1. additionAfter the addition
  2. additionTo this was added, over 15 minutes
  3. stirringThe mixture was stirred for one hour
  4. extractionthe product extracted into ethyl acetate
  5. customThe solvent was removed
  6. filtrationthe product filtered through a pad of silica gel
  7. washeluted with 1:3 ethyl acetate-hexane
  8. washAdditional chromatography over alumina and elution with 1:4 ethyl acetate-hexane
  9. customfollowed by recrystallization from etherhexane and finally from methanol
  10. customgave 0.6 gm of the color
  11. customforming developer

Sources & evidence

ORD record
ord-633728ca8dc342b2ae45c6113c1f2251
Source dataset
uspto-grants-1988_11
Patent number
US04782010

Reaction notes

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