Water → HCID 386098, compound

HRID 1456608Notes

Reaction equation

HRID 1456608 reaction equation
[Si]([O:8][C@H:9]1[C:18]2[C:13](=[CH:14][C:15]([O:27][CH:28]([CH3:30])[CH3:29])=[C:16]3[C:22]([CH2:23][CH2:24][CH3:25])=[CH:21][C:20](=[O:26])[O:19][C:17]3=2)[O:12][C@H:11]([CH3:31])[C@H:10]1[CH3:32])(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O>C1COCC1.[Cl-].[Na+].O>[OH:8][C@H:9]1[C:18]2[C:13](=[CH:14][C:15]([O:27][CH:28]([CH3:30])[CH3:29])=[C:16]3[C:22]([CH2:23][CH2:24][CH3:25])=[CH:21][C:20](=[O:26])[O:19][C:17]3=2)[O:12][C@H:11]([CH3:31])[C@H:10]1[CH3:32]

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 18667260HCID 18667260, compound

Product 1

HCID 386098HCID 386098, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6a (130 mg, 0.29 mmol) in THF (5 mL) was added Bu4NF (1.45 mL, 1M solution in THF) at 0° C. The reaction mixture was stirred at room temperature for 6 h. Water was added (2 mL), followed by brine (2 mL). The solution was extracted with ether (3×5 mL). The combined organic layers were dried (MgSO4), concentrated, and submitted for silica gel chromatography (Solvent B) to obtain 7a (92 mg, 91%) as a syrup: [α]D20 +26.5° (c 1.1, CHCl3); 1H NMR (CDCl3): δ 0.97 (t, 3 H, J=7.3 Hz, --CH2 CH2CH3), 1.08 (d, 3 H, J=7.0 Hz, --CHCH3), 1.37 [d, 9 H, J=6.2 Hz, --CH(CH3)2, CHCH3 ], 1.57 (m, 2 H, --CH2 CH2CH3), 1.70 (m, 1 H, H-9), 2.99 (m, 2 H, --CH2CH2 CH3), 4.22 (m,1 H, H-8), 4.59 [m, 1 H, --CH(CH3)2 ], 4.91 (d, 1 H, J=2.7 Hz, H-10), 5.88 (s, 1 H, H-3), 6.16 (s, 1 H, H-6): 13 C NMR (CDCl3): δ 12.49, 13.84, 18.83, 21.69, 21.74, 23.15, 38.38, 38.89, 61.65, 70.65, 72.87, 96.65, 104.20, 106.18, 110.10, 155.12, 156.36, 158.03, 159.09, 161.07. Anal. Calcd for C20H26O5 : C, 69.34; H, 7.56. Found: C, 69.15; H, 7.93.

Workup

  1. extractionThe solution was extracted with ether (3×5 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-de30bd79e2b64da88ea3094d618e992e
Source dataset
uspto-grants-1998_12
Patent number
US05843990

Reaction notes

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