Acetic Acid → HCID 58687907, compound

HRID 1988573Notes

Reaction equation

HRID 1988573 reaction equation
[N:1]1([C:7]2[O:12][C:11]([C:13]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:14]=3[S:15][C:16]3[CH:17]=[CH:18][C:19]([CH:27]=[O:28])=[CH:20][C:21]=3[CH2:22]4)=[CH:10][C:9](=[O:29])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[OH:28][CH2:27][C:19]1[CH:20]=[C:21]2[C:16]([S:15][C:14]3[C:13]([C:11]4[O:12][C:7]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:8][C:9](=[O:29])[CH:10]=4)=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 5003444Sodium cyanoborohydrideHCID 58687906HCID 58687906, compound

Product 1

HCID 58687907HCID 58687907, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthene-2-carbaldehyde (2)(0.392 g, 0.97 mmol) in ethanol (7 mL) at room temperature was added sodium cyanoborohydride (121 mg, 1.93 mmol), followed by the addition of acetic acid (1 mL). After 5 hours, a second addition of acetic acid (1 mL) was made. After a further 12 hours, the excess borohydride was quenched with acetone. After evaporation in vacuo, saturated NaHCO3 was added, followed by extraction into dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The brown coloured solid was dried under vacuum at 50° C. to give the crude title compound (0.332 g, 84%) which was used without any further purification. m/z (LC-MS, ESP), RT=3.09 min, (M++1)=408.3

Workup

  1. waitAfter a further 12 hours
  2. customthe excess borohydride was quenched with acetone
  3. customAfter evaporation in vacuo, saturated NaHCO3
  4. additionwas added
  5. extractionfollowed by extraction into dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe brown coloured solid was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-3a6ec440699d49bead9bc9ecb44e0a4c
Source dataset
uspto-grants-2010_01
Patent number
US07642254B2

Reaction notes

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