Acetic Anhydride → HCID 13197843, compound

HRID 1594770Notes

Reaction equation

HRID 1594770 reaction equation
OC1[CH:3]=[C:4]2[C:9](=[CH:10]C=1OC)[CH2:8][CH2:7][CH2:6][CH2:5]2.[C:14]([O:17][C:18](=[O:20])[CH3:19])(=O)[CH3:15].C1C[O:24][CH2:23]C1>CN(C)C1C=CN=CC=1>[C:18]([O:17][C:14]1[CH:3]=[C:4]2[C:9](=[CH:10][C:15]=1[O:24][CH3:23])[CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran3×HCID 136994193579-88-22×

Product 1

HCID 13197843HCID 13197843, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
25 °C

Procedure

A 250 mg (1.4 mmol) quantity of 6-hydroxy-7-methoxytetralin was dissolved in 1 mL of dry THF. To the solution of 6-hydroxy-7-methoxytetralin was added 4-dimethylaminopyridine (DMAP, 476 mg, 4.2 mmol) in 6 ml of dry THF and acetic anhydride 446 mg (4.37 mmol) in 1.5 mL, of dry THF. The reaction solution was stirred under a dry atmosphere at 25° C. for 18 hours, after which time the solvent was evaporated to dryness. The resulting residue was dissolved in EtOAc (40 mL) and the EtOAc layer washed with water (2×5 mL), 5% NaHCO3 (aq) (2×5 mL), 1 M HCl (5×5 mL), water (5 mL), and brine (2×5 mL). The organic layer was dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromotography (hexane : EtOAc, 4:1) to give 290 mg (94% yield) of 6-acetoxy-7-methoxytetralin. IR 3003, 2930, 2860, 2840, 1767 (C═O str.), 1619, 1512, 1266, 1219, 1195, 1104, 1026; 1H NMR (CDCl13) δ6.73 (1H, s), 6.66 (1H, s), 3.79 (3H, s, —OCH3), 2.68-2.74 (4H, m), 2.30 (3H, s, —OCOCH3), 1.78 (4H, qn, J=3.25 Hz); 13C NMR (CDCl3) δ6.73 169.3, 148.6, 137.5, 135.3, 129.3, 122.8, 112.8, 55.8, 29.3, 28.4, 23.0, 20.5; LRMS EI m/z 220[M+], 178 [M+, base peak].

Workup

  1. customafter which time the solvent was evaporated to dryness
  2. dissolutionThe resulting residue was dissolved in EtOAc (40 mL)
  3. washthe EtOAc layer washed with water (2×5 mL), 5% NaHCO3 (aq) (2×5 mL), 1 M HCl (5×5 mL), water (5 mL), and brine (2×5 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromotography (hexane : EtOAc, 4:1)

Sources & evidence

ORD record
ord-fa907c78bc154abc88df0cd2fe439ea8
Source dataset
uspto-grants-2001_09
Patent number
US06284789B1

Reaction notes

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