1,3-Dithiane → HCID 86701114, compound

HRID 1396265Notes

Reaction equation

HRID 1396265 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][S:3][CH2:2]1.[Li]CCCC.[CH2:12]([O:19][C@@H:20]1[C@@H:28]([CH:29]=[O:30])[O:27][C@H:26]2[C@H:22]([N:23]=[C:24]([N:31]([CH3:33])[CH3:32])[S:25]2)[C@H:21]1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([O:19][C@@H:20]1[C@@H:28]([C@H:29]([CH:2]2[S:3][CH2:4][CH2:5][CH2:6][S:1]2)[OH:30])[O:27][C@H:26]2[C@H:22]([N:23]=[C:24]([N:31]([CH3:33])[CH3:32])[S:25]2)[C@H:21]1[O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 104511,3-DithianeHCID 87687100HCID 87687100, compoundHCID 178418339Butyllithium

Product 1

HCID 86701114HCID 86701114, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-dithiane (14.1 g, 117 mmol) in THF (100 mL) was treated with n-BuLi (44.9 mL, 112 mmol, 2.5M in hexane) at 0° C. for 1 hour, followed by the addition of a solution of the above aldehyde 95 in THF (20 mL) at −50° C. After kept additional 1 hour at 0° C., the reaction was quenched by saturated aqueous NH4Cl (150 mL) and extracted with ethyl acetate (3×80 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 20%-50% ethyl acetate in petroleum to afford the title compound as a yellow syrup (6.4 g, 62%, two epimers' ratio is 1:1 by 1H NMR); (ES, m/z) [M+H]+ 547.0; 1H NMR (300 MHz, CDCl3) δ 7.28-7.44 (m, 10H), 6.33 (d, J=6.6 Hz, 1H), 4.63-4.84 (m, 4H), 4.52-4.58 (m, 1H), 4.12-4.15 (m, 1H), 3.98-4.05 (m, 3H), 3.82-3.85 (m, 1H), 2.99 (s, 6H), 2.80-2.87 (m, 1H), 2.61-2.68 (m, 3H), 1.65-1.69 (m, 2H).

Workup

  1. customthe reaction was quenched by saturated aqueous NH4Cl (150 mL)
  2. extractionextracted with ethyl acetate (3×80 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by a silica gel column
  8. washeluted with 20%-50% ethyl acetate in petroleum

Sources & evidence

ORD record
ord-0fb728475a9443dfa0c32cc36f52b45d
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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