Hydrochloric Acid → HCID 20464113, compound

HRID 325791Notes

Reaction equation

HRID 325791 reaction equation
[C:1]([O:7][C:8]1[CH:42]=[CH:41][C:11]([C:12]([O:14][C:15]2[CH:16]=[C:17]([C:37](=[O:40])[CH2:38][Br:39])[CH:18]=[C:19]([O:21][C:22](=[O:36])[C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:25][CH:24]=3)[CH:20]=2)=[O:13])=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[BH4-].[Na+].Cl>O1CCOCC1.O>[C:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([O:21][C:19]2[CH:18]=[C:17]([CH:37]([OH:40])[CH2:38][Br:39])[CH:16]=[C:15]([O:14][C:12](=[O:13])[C:11]3[CH:41]=[CH:42][C:8]([O:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:9][CH:10]=3)[CH:20]=2)=[O:36])=[CH:28][CH:27]=1)(=[O:35])[C:31]([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20464115HCID 20464115, compound

Product 1

HCID 20464113HCID 20464113, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7.8 g (0.012 moles) of 3',5'-bis-(4-pivaloyloxybenzoyloxy)-2-bromoacetophenone in 200 ml of dioxane and 40 ml of water was added portionally 0.45 g (0.012 moles) of NaBH4 dissolved in 30 ml of water. After each addition pH was adjusted with 1 N HCl so that the pH of the reacting mixture never exceeded pH 7. The mixture was stirred at ambient temperature for 1 h, whereafter the solution was evaporated to dryness and the residue taken up in diethyl ether. The ether phase was washed with water, dried over MgSO4 and then evaporated to dryness to yield a crystalline residue. The identity of the product was confirmed with NMR.

Workup

  1. customwas evaporated to dryness
  2. washThe ether phase was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customto yield a crystalline residue

Sources & evidence

ORD record
ord-41a2ad97589d42cc9919d24d7ca8022c
Source dataset
uspto-grants-1984_04
Patent number
US04442300

Reaction notes

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