Water → HCID 22861101, compound

HRID 439853Notes

Reaction equation

HRID 439853 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH:6]2[CH2:13][C:14]3[C:19]([CH:5]12)=[CH:18][C:17]([CH3:21])(C)[CH:16]([O:22]C)[CH:15]=3)(=O)[CH3:2].B(Br)(Br)Br.[OH2:28].Cl[CH2:30]Cl>>[C:1]([N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C@H:6]2[CH2:13][C:14]3[C:19]([C@@H:5]12)=[CH:18][C:17]([CH3:21])=[C:16]([OH:22])[C:15]=3[CH3:30])(=[O:28])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 22408507HCID 22408507, compound

Product 1

HCID 22861101HCID 22861101, compound

Procedure

Under anhydrous conditions a solution of 5-acetyl-4b,5,9b,10-tetrahydro-2-methoxy-3,3-dimethylindeno[1,2-b]indole (109 mg, 0.35 mmol) in dichloromethane (1 cm3) was cooled to -78° C., and a solution of boron tribromide in dichloromethane (0.7 cm3 of 1M solution) added. The reaction was allowed to warm to room temperature, and stirred for 90 minutes, where-upon water (5 cm3) was cautiously added. After stirring for a further 10 minutes, the mixture was diluted, and extracted with dichloromethane. The combined dichloromethane extracts were dried (Na2SO4) and filtered through a pad of "flash" silica eluting further with 30% EtOAc/60°-80° petrol. Removal of solvent yielded a colourless solid. Yield: 96 mg, 94%. M.p. 205° C. (dec). 1H NMR (CDCl3) δ: [mixture of E/Z isomers] 8.06 (1/2H, d, J=7.1 Hz), 8.05-7.00 (41/2H, m), 4.23 and 5.75 (1H, d, J=8.1 and 7.5 Hz), 4.6 (1H, br), 4.22-4.08 (1H,2×ddd), 3.45-3.26 (1H, m), 3.25-3.05 (1H, 2×dd), 2.63 and 2.52 (3H, s), 2.20 and 2.17 (3H, s), 2.13 and 2.11 (3H, s).

Workup

  1. stirringAfter stirring for a further 10 minutes
  2. additionthe mixture was diluted
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  5. filtrationfiltered through a pad of "flash" silica eluting further with 30% EtOAc/60°-80° petrol
  6. customRemoval of solvent
  7. customyielded a colourless solid

Sources & evidence

ORD record
ord-fcc2a51d79b94dcca1cc5543e77b5e22
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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