Boron tribromide → HCID 69151947, compound

HRID 1093940Notes

Reaction equation

HRID 1093940 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:6]=[C:5](OC)[C:4]=1[C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:22]([O:24]C)=[O:23].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:6]=[C:5]2[C:4]=1[C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:22](=[O:24])[O:23]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66640999HCID 66640999, compound

Product 1

HCID 69151947HCID 69151947, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

260 mg (0.75 mmol) of methyl trans-2-(2,6-dimethoxy-4-pentylphenyl)cyclo-hexanecarboxylate were initially introduced in 10 ml of dichloromethane, and 191 μl (2 mmol) of boron tribromide were added at −70° C. After 20 min, the cooling was removed, and the batch was hydrolysed at 0° C. using sat. sodium hydrogencarbonate soln. The mixture was extracted with dichloromethane, dried over sodium sulfate and evaporated. Chromatography with heptane/ethyl acetate (7:1) gave 100 mg (45%) of (6aR*,10aR*)-1-hydroxy-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-6-one as a colourless solid.

Workup

  1. customthe cooling was removed
  2. customwas hydrolysed at 0° C.
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-a9125a74c39e4c19bf5401a33ae0165e
Source dataset
uspto-grants-2012_03
Patent number
US08133887B2

Reaction notes

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