Sodium Sulfide → HCID 53241771, compound

HRID 422127Notes

Reaction equation

HRID 422127 reaction equation
[S-2].[Na+].[Na+].C[O:5][C:6]1[CH:23]=[C:22]2[C:9]([C@@:10]3([CH3:27])[C@H:19]([CH2:20][O:21]2)[C@:18]2([CH3:24])[C@H:13]([C:14]([CH3:26])([CH3:25])[CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]3)=[C:8]([CH3:28])[CH:7]=1>CN1C(=O)CCC1>[CH3:27][C@@:10]12[CH2:11][CH2:12][C@@H:13]3[C@:18]([CH3:24])([CH2:17][CH2:16][CH2:15][C:14]3([CH3:25])[CH3:26])[C@H:19]1[CH2:20][O:21][C:22]1[C:9]2=[C:8]([CH3:28])[CH:7]=[C:6]([OH:5])[CH:23]=1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 53241659HCID 53241659, compound

Product 1

HCID 53241771HCID 53241771, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium sulfide (0.14 g, 1.17 mmol) was added to a solution of (1R,10R,11S,16S)-5-methoxy-1,3,11,15,15-pentamethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 5) (0.08 g, 0.2 mmol) in anhydrous NMP (1.6 mL) in a microwave vessel. The reaction vessel was sealed and placed in a CEM-Discovery reactor and irradiated at 180° C. for 20 min. The reaction mixture was allowed to cool to room temperature and then quenched with 2 M HCl and ethyl acetate. The organic layer was separated, washed with water and concentrated to dryness. The crude product was purified by flash chromatography (Hexanes/EtOAc, 9:1) to yield (1R,10R,11S,16S)-1,3,11,15,15-pentamethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol (Compound No. 6) (0.022 g, 29% yield) as a white solid. 1H NMR (CDCl3): δ 6.08 (m, 2H), 4.43 (s, 1H), 4.30 (m, 1H), 4.08 (m, 1H), 2.80 (m, 1H), 2.40 (s, 3H), 1.40-1.78 (m, 8H), 1.36 (s, 3H), 0.98-1.28 (m, 3H), 0.92 (s, 3H), 0.88 (s, 3H), 0.84 (s, 3H). MS m/z 329 (C22H32O2+H+).

Workup

  1. customThe reaction vessel was sealed
  2. customplaced in a CEM-Discovery reactor
  3. customirradiated at 180° C. for 20 min
  4. customquenched with 2 M HCl and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by flash chromatography (Hexanes/EtOAc, 9:1)

Sources & evidence

ORD record
ord-f82dc303aedf4f0aace66c47e5799f58
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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