Tetrahydrofuran → (1R*,2R*)-Acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester

HRID 28792

Reaction equation

HRID 28792 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Cl.C(N([CH2:12][CH3:13])CC)C.[CH2:14]1[CH2:18][O:17][CH2:16][CH2:15]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[OH:17][C@@H:16]1[C:12]2[C:13](=[CH:18][CH:14]=[CH:15][CH:16]=2)[CH:18]=[CH:14][C@H:15]1[O:3][C:1](=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11130Triethylamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 9837127(1R*,2R*)-Acetic acid 1-hydroxy-1,2-dihydro-naphthalen-2-yl-ester

Reagents, catalysts & solvents 1

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Procedure

To a flame dried round bottom flask, [Rh(COD)Cl]2 (4.3 mg, 0.008 mmol DPPF (9.6 mg, 0.017 mmol),1 (50 mg, 1.39 mmol), and sodium acetate (142 mg, 1.74 mmol) were added followed by addition of THF (2 mL) and triethylamine hydrochloride (239 mg, 1.74 mmol). The mixture was heated at reflux for 3 hours and the solvents were removed in vacuio. The resulting mixture was purified by flash chromatography (30% ethyl acetate in hexanes) to give 2 as a crystalline solid (41 mg), 63%). Rf=0.26 on silica gel (20% ethyl acetate:hexanes); mp 67-68° (Et2O); IR (KBr, cm−1) 1H NMR (400 MHz, CDCl3) δ 7.54-7.53 (1H, m), 7.29-7.24 (2H, m), 7.10-7.08 (1H, m), 6.50 (1H, dd, J=3.9, 1.3 Hz), 5.85 (1H, dd, J=9.9, 3.1 Hz), 5.59 (1H, ddd, J=9.0, 2.8, 1.9 Hz), 4.92 (1H, d, J=9.0 Hz), 2.64 (1H, s), 2.12 (3H, s); 13C NMR (400 MHz, CDCl3) δ 171.3, 135.2, 131.5, 129.5, 128.3, 126.7, 126.0, 125.4, 75.3, 71.7, 21.2. HRMS calcd for C12H12O3 (M+): 204.0786. Found: 204.0791.

Workup

  1. customTo a flame dried round bottom flask
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 hours
  4. customthe solvents were removed in vacuio
  5. customThe resulting mixture was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-88e7ded5a61e46328892f889f67ed6cb
Source dataset
uspto-grants-2008_09
Patent number
US07420003B2

Linked notes

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