HCID 58238515, compound → HCID 58238512, compound

HRID 1042514Notes

Reaction equation

HRID 1042514 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:23]2[C:24]([O:35]C)=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)C1C=CC=CC=1>C(#N)C>[CH3:1][O:8][C:9]1[C:14]([CH:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:24]=2[OH:35])=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 1

HCID 58238515HCID 58238515, compound

Product 1

HCID 58238512HCID 58238512, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of crude 8 (2.2 g) in acetonitrile (50 mL) was treated with 50% aqueous hypophsophorous acid (22 mL) and stirred at reflux overnight. After cooling, the acetonitrile was removed on a rotary evaporator. The residue was taken in ethyl acetate (150 mL) and washed with water (2×100 mL), saturated sodium bicarbonate (100 mL) and water (100 mL). The organic layer was dried over sodium sulfate and stripped. The residue was chromatographed on silica (60 g) with 0.5% ethyl acetate in hexane (3 L). The relevant fractions were stripped and the residue was triturated with a little ethanol. The solid was collected by filtration, washed with cold ethanol and dried in a vacuum oven at 65° C. to produce pure B2 (0.69 g, 37% over 2 steps).

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customthe acetonitrile was removed on a rotary evaporator
  4. washwashed with water (2×100 mL), saturated sodium bicarbonate (100 mL) and water (100 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customThe residue was chromatographed on silica (60 g) with 0.5% ethyl acetate in hexane (3 L)
  7. customthe residue was triturated with a little ethanol
  8. filtrationThe solid was collected by filtration
  9. washwashed with cold ethanol
  10. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-70fcb16fa2724ea98d0662a02b7126e1
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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