Sodium Hydroxide → HCID 9959087, compound

HRID 1954295Notes

Reaction equation

HRID 1954295 reaction equation
[CH3:1][C:2]1[O:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([OH:23])=[C:17]([CH2:24][CH3:25])[CH:16]=4)[C:4]=2[C:3]=1[CH3:26])[CH:12]=[CH:11][CH:10]=[CH:9]3.[OH-].[Na+].Cl[S:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=1)(=[O:32])=[O:31]>C1COCC1>[CH3:1][C:2]1[O:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([O:23][S:30]([C:33]5[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[C:35]([OH:42])[CH:34]=5)(=[O:32])=[O:31])=[C:17]([CH2:24][CH3:25])[CH:16]=4)[C:4]=2[C:3]=1[CH3:26])[CH:12]=[CH:11][CH:10]=[CH:9]3

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide3×HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acid2×HCID 22665460HCID 22665460, compound

Product 1

HCID 9959087HCID 9959087, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

At ambient temperature, to a stirred suspension containing 4-(2, 3-dimethyl-naphtho[2,3-b]furan-4-yl)-2,6-diethyl-phenol (0.317 g, 0.919 mmol) and 0.O1M aq. Borax (6 mL) in THF (9 mL) was added 2.5N NaOH (0.397 mL). To the reaction was added dropwise a solution of 4-chlorosulphonyl-2-hydroxybenzoic acid (0.653 g, 2.76 mmol) in THF (12 mL) while maintaining the pH at 10 with the simultaneous addition of 2.5N NaOH. After 48 h, additional 4-chlorosulphonyl-2-hydroxybenzoic acid (0.440 g, 1.86 mmol) in THF (12 mL) was added dropwise while maintaining the pH at 10 with the simultaneous addition of 2.5N NaOH and the reaction was stirred for an additional 48 h. The reaction was quenched with 1N HCl and extracted with ether. The combined ethereal extracts were washed with brine (1×), dried (Na2SO4) and concentrated. Purification on 2% H3PO4 /MeOH treated silica gel eluting with 2% EtOAc/hexane followed by recrystallization (EtOAc/hexane) gave 95 mg (19%) of the title compound as an off white solid, mp 222-227° C. 1H NMR (DMSO-d6) δ 1.09 (t, 6 H), 1.55 (s, 3 H), 2.40 (s, 3 H), 2.55-2.60 (m, 4 H), 7.21 (s, 2 H), 7.37-7.39 (m, 1 H), 7.43-7.49 (m, 3 H), 7.53 (d of d, 1 H), 7.99 (s, 1 H), 8.01-8.04 (m, 1 H), 8.08 (d, 1 H). mass spectrum (-ESI) m/z 543 (M-H). Anal. Calcd. for C31H28O7S.0.5H2O: C, 67.25; H, 5.28; N, 0.00. Found: C, 67.14; H, 5.21; N, 0.08.

Workup

  1. temperaturewhile maintaining the pH at 10
  2. temperaturewhile maintaining the pH at 10
  3. customThe reaction was quenched with 1N HCl
  4. extractionextracted with ether
  5. washThe combined ethereal extracts were washed with brine (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification on 2% H3PO4 /MeOH
  9. additiontreated silica gel eluting with 2% EtOAc/hexane
  10. customfollowed by recrystallization (EtOAc/hexane)

Sources & evidence

ORD record
ord-728cf6495e6c48a6a7268e4fc60d9985
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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