Water → HCID 22860355, compound

HRID 1721307Notes

Reaction equation

HRID 1721307 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-f7eb6530048d45828abc3a0f2f58ba18
Source dataset
uspto-grants-1996_04
Patent number
US05510340

Reaction notes

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