Sodium Dithionite → HCID 21946139, compound

HRID 1047346Notes

Reaction equation

HRID 1047346 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])[N+:12]([O-])=[C:11]1[C:6](=[CH:7][C:8](=[O:23])[CH:9]=[CH:10]1)[O:5]2.S(S([O-])=O)([O-])=O.[Na+].[Na+]>[OH-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[N:12]=[C:11]1[C:6](=[CH:7][C:8](=[O:23])[CH:9]=[CH:10]1)[O:5]2

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 21946118HCID 21946118, compound

Product 1

HCID 21946139HCID 21946139, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl ester (10a) (22.83 g, 72.4 mmol) was dissolved in 400 ml of 0.5 M aqueous sodium hydroxide and the solution was stirred for 1 h. A solution of sodium dithionite solution (200 ml, 100 mmol) was added and reaction mixture was stirred for additional 15 minutes. To precipitate the product 3 M hydrochloric acid (80 ml) was carefully added and resultant suspension was stirred for 10 min and centrifuged. The supernatant was decanted and the residue was re-suspended in ˜800 ml of water and centrifuged again. This operation was repeated one more time. Final supernatant had pH of 3-4. The centrifuged material was dried under vacuum overnight at 40° C. to afford 14.12 g (68%) of desired product (11a) as a brown solid. 1H NMR (CD3OD, +40° C.): δ 7.64 (d, J=9.0 Hz, 1H), 7.39 (s, 1H), 6.89 (d, J=9.0 Hz, 1H), 6.74 (s, 1H), 6.34 (s, 1H), 2.63 (m, 2H), 2.51 (m, 2H).

Workup

  1. customreaction mixture
  2. stirringwas stirred for additional 15 minutes
  3. customTo precipitate the product 3 M hydrochloric acid (80 ml)
  4. additionwas carefully added
  5. stirringresultant suspension was stirred for 10 min
  6. customThe supernatant was decanted
  7. customThe centrifuged material was dried under vacuum overnight at 40° C.

Sources & evidence

ORD record
ord-f349cd0f9df840b092148140e406ec35
Source dataset
uspto-grants-2013_10
Patent number
US08569516B2

Reaction notes

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