Ethyl Acetate → HCID 66652098, compound

HRID 418965Notes

Reaction equation

HRID 418965 reaction equation
[Li][CH2:2]CCC.[OH:6][C:7]1[CH:8]=[C:9]([CH:27]=O)[C:10]2[CH2:11][CH:12]([C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[CH:13]3[CH2:19][CH2:18][CH2:17][CH:14]3[C:15]=2[CH:16]=1.C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH:12]2[CH2:11][C:10]3[C:15](=[CH:16][C:7]([OH:6])=[CH:8][C:9]=3[CH:27]=[CH2:2])[CH:14]3[CH2:17][CH2:18][CH2:19][CH:13]23)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 72309404HCID 72309404, compoundHCID 178418339Butyllithium

Product 1

HCID 66652098HCID 66652098, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Combine BuLi (0.1 ml, 1.6M, 0.16 mmol), methyltriphenylphosphonium bromide (0.063 g, 0.175 mmol) and tetrahydrofuran (1.0 ml) and stir 15 minutes. Add 8-Hydroxy-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalene-6-carbaldehyde (0.012 g, 0.04 mmol) in tetrahydrofuran (1.0 ml) and stir 30 minutes. Take into ethyl acetate and wash with ammonium chloride solution solution, then brine. Dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 33% EtOAC/hexanes, the titled compound (0.006 g, 50%). 1H NMR (CD3OD) 7.15 (d, J=8.4, Hz, 2H), 7.04 (dd, J=11 and 6 Hz, 1H), 6.75 (m, 3H), 3.4 (m, 1H), 3.0 (m, 1H), 2.85 (m, 2H), 2.55(m, 1H) 2.2 (m, 1H), 1.6-1.2. MS m/z 305 (M−1).

Workup

  1. washwash with ammonium chloride solution solution
  2. dry with materialDry over anhydrous sodium sulfate
  3. concentrationconcentrate to a residue which
  4. customyields
  5. customafter separation on silica gel with 33% EtOAC/hexanes

Sources & evidence

ORD record
ord-d48e1c7f6fb441c4b637f07dd455e518
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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