TBAF tetrahydrofuran → HCID 57814824, compound

HRID 1254176Notes

Reaction equation

HRID 1254176 reaction equation
[Si]([O:8][C@H:9]([CH3:42])[CH2:10][CH2:11][CH2:12][C@H:13]([OH:41])/[CH:14]=[CH:15]/[C@H:16]1[C@H:20]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:19][C@@H:18]([Cl:28])[C@@H:17]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH2:39][CH3:40])=[O:36])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[Cl:28][C@H:18]1[C@H:17]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH2:39][CH3:40])=[O:36])[C@@H:16](/[CH:15]=[CH:14]/[C@@H:13]([OH:41])[CH2:12][CH2:11][CH2:10][C@H:9]([OH:8])[CH3:42])[C@H:20]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:19]1

Participants

3

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 57814803HCID 57814803, compound

Product 1

HCID 57814824HCID 57814824, compoundYield 84.3%

Procedure

A solution of silyl ether 14 (316 mg, 0.50 mmol) was stirred at 35° C. with 2 mL of 1.0M TBAF/THF in a vial for 9.5 h. TLC indicated starting material was mostly desilylated and the reaction was concentrated in vacuo. The residual crude products were taken up in 50 mL of ethyl acetate and washed sequentially with saturated ammonium chloride (50 mL), brine (50 mL), and dried over 10 g of anhydrous sodium sulfate. The mixture was filtered and concentrated in vacuo. The residual products were purified by flash column chromatography on 40 g of silica gel eluted in 1:1 hexanes:EtOAc, then straight EtOAc. Combination of appropriate fractions and removal of the solvents yielded 218 mg (84%) of diol 15 as an oil; 1H NMR (CDCl3): 0.94 (t, J=7.5 Hz, 31H), 1.18 (d, J=6.3 Hz, 3H), 1.31 (m, 6H), 1.42-1.90 (m, 19H), 2.10-2.50 (m, 7H), 3.48 (m, 1H), 3.72-4.16 (m, 7H), 4.64 (dt, 1H), 5.57 (m, 2H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. washwashed sequentially with saturated ammonium chloride (50 mL), brine (50 mL)
  3. dry with materialdried over 10 g of anhydrous sodium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customThe residual products were purified by flash column chromatography on 40 g of silica gel
  7. washeluted in 1:1 hexanes
  8. customCombination of appropriate fractions and removal of the solvents

Sources & evidence

ORD record
ord-823ceebc23dc48cca8114cd94f67e932
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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