Benzoic Acid → HCID 22218642, compound

HRID 1795493Notes

Reaction equation

HRID 1795493 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C1C=CC=CC=1.[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[C@@H:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C@H:41]([OH:48])[CH2:40]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41](=[O:48])[CH2:40]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59041337HCID 59041337, compound2×

Product 1

HCID 22218642HCID 22218642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenylphosphine (1.44 g, 5.49 mmol) and benzoic acid (0.60 g, 4.91 mmol) were added to a solution of cis-3-(2-naphthyl)-indan-1-ol, 6a and 6b (0.645 g, 2.48 mmol) in anhydrous THF (20 mL). The reaction was treated dropwise with a solution of DEAD in THF (4.95 M, 1 mL) then stirred under nitrogen atmosphere at room temperature. After 3 h, the reaction solution was directly filtered through a pad of silica and condensed. The resulting residue was purified by radial chromatography (4 mm plate, 10% ethyl acetate/hexanes) yielding a mixture of enantiomers 8a and 8b as an off-white solid (0.72 g, 80%): Rf=0.46 in 10% ethyl acetate/hexanes; 1H-NMR (CDCl3) δ 8.08–8.05 (m, 2H), 7.84–7.78 (m, 3H), 7.71 (bs, 1H), 7.58–7.41 (m, 4H), 7.35–7.29 (m, 2H), 7.24 (dd, 2H, J=5.7, 2.7), 7.07–7.04 (m, 1H), 6.62 (dd, 1H, J=6.3, 1.9), 4.88 (t, 1H, J=7.7), 2.83 (ddd, 1H, J=2.2, 7.7, 14.6), 2.69–2.60 (ddd, 1H, J=6.6, 7.98, 14.6).

Workup

  1. filtrationthe reaction solution was directly filtered through a pad of silica and condensed
  2. customThe resulting residue was purified by radial chromatography (4 mm plate, 10% ethyl acetate/hexanes)
  3. customyielding

Sources & evidence

ORD record
ord-d00e89c4cb484ea190c609f21132198f
Source dataset
uspto-grants-2006_04
Patent number
US07026516B2

Reaction notes

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