Dichloromethane → HCID 86654186, compound

HRID 422158Notes

Reaction equation

HRID 422158 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21]C)[CH:18]=[C:17]2[C:4]=1[C@H:5]1[C@H:14]([CH2:15][S:16]2(=[O:24])=[O:23])[C@:13]2([CH3:25])[C@H:8]([C:9]([CH3:27])([CH3:26])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.C(Cl)Cl.B(Br)(Br)Br>>[OH:21][C:19]1[CH:18]=[C:17]2[C:4]([C@H:5]3[C@H:14]([CH2:15][S:16]2(=[O:23])=[O:24])[C@:13]2([CH3:25])[C@H:8]([C:9]([CH3:26])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]3)=[C:3]([O:2][CH3:1])[CH:20]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86654187HCID 86654187, compound

Product 1

HCID 86654186HCID 86654186, compoundYield 59.3%

Procedure

To a solution of (1R,10S,11S,16S)-3,5-dimethoxy-11,15,15-trimethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (23) (7.6 g, 18.7 mmol) in CH2Cl2 (250 mL) BBr3 (1 M in CH2Cl2 18.7 mL, 18.7 mmol) was added dropwise at room temperature under N2. The mixture was stirred at room temperature for 18 h. Additional BBr3 (1 M in CH2Cl2 18.7 mL, 18.7 mmol) was added to the reaction and stirring continued for another 6 h. The mixture was poured onto crushed ice and the organic layer was separated and concentrated to dryness. The residue was purified by flash chromatography on silica gel (Hexanes/EtOAc, 3:1) to yield (1R,10S,11S,16S)-5-hydroxy-3-methoxy-11,15,15-trimethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (57) (4.2 g, 57%) as a pale brown solid.

Workup

  1. stirringstirring
  2. waitcontinued for another 6 h
  3. additionThe mixture was poured
  4. customonto crushed ice
  5. customthe organic layer was separated
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by flash chromatography on silica gel (Hexanes/EtOAc, 3:1)

Sources & evidence

ORD record
ord-bbb1223f4d604afb8102b1dac9f1cc9c
Source dataset
uspto-grants-2012_01
Patent number
US08101605B2

Reaction notes

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