Sodium Hydroxide → HCID 86742441, compound

HRID 622718Notes

Reaction equation

HRID 622718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[CH:18]([OH:27])[CH2:19][CH:20]([OH:26])[CH2:21][C:22](OC)=[O:23])=[CH:4][C:3]=1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2/[CH:16]=[CH:17]/[C@@H:18]2[O:27][C:22](=[O:23])[CH2:21][C@@H:20]([OH:26])[CH2:19]2)=[CH:4][C:3]=1[CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13553301HCID 13553301, compound

Product 1

HCID 86742441HCID 86742441, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound (1h) (900 mg 1.7 mmol), 1 N NaOH (2.5 mL, 2.5 mmol) and MeOH (15 mL) was stirred at 25° C. for 1 hour. The reaction mixture was evaporated in vacuo at 25° C. and the residue was dissolved in H2O (100 mL). The reaction solvent was acidified with 12 N HCl (1 mL) and extracted with Et2O (100 mL). The organic extract was washed with H2O (2×100 mL), dried over MgSO4, filtered, evaporated and the residual crude dihydroxy acid was dissolved in toluene (75 mL) and heated at reflux in a Dean-Stark apparatus. After 3 hours the toluene was removed in vacuo leaving the crude compound (1i) as a thick yellow oil. The oil was chromatographed on silica gel. Elution with CH2Cl2 -acetone (19:1, v=v) to provide the compound (1i) as a pale yellow oil, homogenous by HPLC [time of elution was 3.72 minutes with a flow rate of 4 mL/minutes using 10% isopropanol/hexane on a Whatman Partisil PXS 10/25 PAC column]; NMR 0.139 (6H, s), 0.946 (9H, s), 1.61-1.84 (2H, m), 2.345 (6H, s), 2.45-2.75 (2H, m), 3.947-3.994 (H, m), 4.81 (2H, m), 5.096-5.134 (H, m), 5.30 (H, dd, J=7 and 16 Hz), 6.50 (H, d, J=16 Hz), 6.938-7.338 (6H, m).

Workup

  1. customThe reaction mixture was evaporated in vacuo at 25° C.
  2. dissolutionthe residue was dissolved in H2O (100 mL)
  3. extractionextracted with Et2O (100 mL)
  4. extractionThe organic extract
  5. washwas washed with H2O (2×100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionthe residual crude dihydroxy acid was dissolved in toluene (75 mL)
  10. temperatureheated
  11. temperatureat reflux in a Dean-Stark apparatus
  12. customAfter 3 hours the toluene was removed in vacuo
  13. customleaving the crude compound (1i) as a thick yellow oil
  14. customThe oil was chromatographed on silica gel
  15. washElution with CH2Cl2 -acetone (19:1, v=v)

Sources & evidence

ORD record
ord-eb0d3e45c5b043e1870cefe9fd3165fd
Source dataset
uspto-grants-1988_09
Patent number
US04772626

Reaction notes

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