Water → HCID 22860355, compound

HRID 2293938Notes

Reaction equation

HRID 2293938 reaction equation
C([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:7]([CH2:8][CH2:9][C:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C:11]=3[C@H:12]([O:32][CH3:33])[CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=O)C.C1COCC1.[OH-].[Na+].O>CO>[CH3:33][O:32][C@H:12]1[C:11]2[C@:23]([CH3:31])([CH2:24][CH2:25][C@H:26]3[C:10]=2[CH2:9][CH2:8][C@@H:7]2[C@:27]3([CH3:30])[CH2:28][CH2:29][C@H:5]([OH:4])[CH2:6]2)[C@@H:14]([C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67706218HCID 67706218, compound

Product 1

HCID 22860355HCID 22860355, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 30 (0.070 g, 0.15 mmol) dissolved in methanol (0.8 mL) and THF (0.4 mL) was added 2N sodium hydroxide (0.2 mL) and the reaction mixture was stirred at ambient temperature for 1 h. Some starting material was still present and the reaction mixture was stirred for an additional 2 h at 50° C. To the reaction mixture was added water (~10 mL). The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water and saline and dried over sodium sulfate. Evaporation of the solvent afforded a white solid that was purified on a silica gel flash column (1×10 cm) and eluted with ethyl acetate/dichloromethane (1:9). Yield of pure compound 31, 0.057 g (89%) mp 127°-128° C. 1H NMR: δ4.21 (dd, 1H, J=6.5, 7.6 Hz), 3.67-3.59 (m, 1H), 3.27 (s, 3H) 2.72-2.68 (m, 1H). 2.26 (ddd, 1H, J=8.0, 8.1, 13.2 Hz), 0.98 (s, 3H), 0.93 (d, 3H, J=6.6 Hz), 0.87 (d, 3H, J=6.7), 0.867 (d, 3H, J=6.6 Hz), 0.74 (s, 3H). IR: 3263, 1336, 1283, 1212, 1131, 1092, 1041. EIMS (m/z): 416.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 h at 50° C
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic phases were washed with water and saline
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customafforded a white solid
  7. customthat was purified on a silica gel flash column (1×10 cm)
  8. washeluted with ethyl acetate/dichloromethane (1:9)

Sources & evidence

ORD record
ord-dc2a64ceaf7e4844b6b9776c407d2d1d
Source dataset
uspto-grants-1997_11
Patent number
US05688780

Reaction notes

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