Tin tetrachloride → HCID 53241986, compound

HRID 422143Notes

Reaction equation

HRID 422143 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([O:26][CH3:27])[CH:25]=1)[O:6][CH2:7][C@@H:8]1[C@:17]2([CH3:18])[C@H:12]([C:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10][C@@:9]1([CH3:22])O.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[CH3:27][O:26][C:24]1[CH:25]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:23]=1[C@@:9]1([CH3:22])[C@H:8]([CH2:7][O:6]2)[C@:17]2([CH3:18])[C@H:12]([C:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 58294812(1S,2R,4aS,8aS)-1-(3,5-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

Product 1

HCID 53241986HCID 53241986, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (1S,2R,4aS,8aS)-1-(3,5-dimethoxyphenoxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (37) (0.68 g, 1.8 mmol) in CH2Cl2 (20 mL), cooled to −78° C., a solution of SnCl4 (1 mL, 8 mmol) in CH2Cl2 (10 mL) was added dropwise. The temperature was maintained at −78° C. for 4 h then the mixture was allowed to warm to room temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 6:1) gave (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 38) (0.49 g, 76%) as a colourless oil. 1H NMR (CDCl3): δ 6.00 (d, 1H), 5.95 (d, 1H), 4.21 (m, 1H), 3.95 (t, 1H), 3.72 (d, 6H), 3.00 (m, 1H), 1.80-0.95 (m, 13H), 0.90 (s, 3H), 0.88 (m, 1H), 0.83 (s, 3H), 0.80 (s, 3H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (Hexanes/EtOAc, 6:1)

Sources & evidence

ORD record
ord-2732efc2260a4a548bce54bfc19a1773
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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