TBAF tetrahydrofuran → HCID 57814800, compound

HRID 1254170Notes

Reaction equation

HRID 1254170 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]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[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]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH:39]=[CH2:40])=[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 57814810HCID 57814810, compound

Product 1

HCID 57814800HCID 57814800, compoundYield 79.3%

Procedure

A solution of silyl ether 7 (270 mg, 0.43 mmol) was stirred at 30° C. with 2 mL (2 mmol) of 1.0M TBAF/THF in a vial for 20 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 20 g of silica gel eluted in 1:1 hexanes:EtOAc, then straight EtOAc. Combination of appropriate fractions and removal of the solvents yielded 175 mg (79%) of pure diol 8 as an oil; 1H NMR (CDCl3): 1.18 (d, J=6 Hz, 3H), 1.38-1.84 (m, 13H), 1.91 (m, 1H), 2.00-2.40 (m, 11H), 3.47 (m, 1H), 3.81 (m, 2H), 3.99 (m, 1H), 4.09 (m, 2H), 4.54-4.72 (m, 3H), 5.21-5.66 (m, 6H), 5.92 (m, 1H).

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 20 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-8485370d33c84de79c8d81fc0515adbe
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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