Water → HCID 68857927, compound

HRID 722423Notes

Reaction equation

HRID 722423 reaction equation
[CH2:1]([C@@:4]12[C:17]3[C:12](=[CH:13][C:14]([O:18]C)=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:20])[CH2:6][CH2:5]2)[CH:2]=[CH2:3].B(Br)(Br)Br.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([C@@:4]12[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]1=[CH:8][C:7](=[O:20])[CH2:6][CH2:5]2)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68835490HCID 68835490, compound

Product 1

HCID 68857927HCID 68857927, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4aR)-4a-allyl-7-methoxy-4,4a,9,10-tetrahydro-3H-phenanthren-2-one (15.0 grams, 55.9 mmol) in methylene chloride (350 mL) at −78° C. was added dropwise boron tribromide (10.6 mL, 112 mmol). The mixture was allowed to warm to 0° C. over 5 hours and was then poured onto a mixture of ice and water. Solid sodium bicarbonate was carefully added to neutralize the mixture which was then extracted with ethyl acetate. After washing with brine, the organic extract was dried (MgSO4) and concentrated under vacuum. The title compound (11.0 grams, 53%) was isolated by flash chromatography eluting with 5 to 10% ethyl acetate in methylene chloride. 1H NMR (CDCl3): δ 7.14 (d, J=8.5 Hz, 1 H), 6.72 (dd, J=2.7, 8.5 Hz, 1 H), 6.58 (d, J=2.7 Hz, 1 H), 5.94 (s, 1 H), 5.62–5.54 (m, 1 H), 5.03–4.98 (m, 2 H), 4.85 (br s, 1 H), 2.95–2.91 (m, 1 H), 2.85–2.63 (m, 5 H), 2.53–2.40 (m, 3 H), 2.08–1.99 (m, 1 H).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washAfter washing with brine
  3. extractionthe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-20e9214f6cbe44259d88912d2ef6d996
Source dataset
uspto-grants-2006_11
Patent number
US07138406B2

Reaction notes

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