Pyridine → [(3-Acetoxyphenyl)methoxymethylene]adamantane

HRID 974440

Reaction equation

HRID 974440 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH:10]=[C:11]2[CH:18]3[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:20][CH:12]2[CH2:13]4)[CH2:17]3)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:29])[CH3:28].C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[C:27]([O:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH:10]=[C:11]2[CH:12]3[CH2:20][CH:16]4[CH2:15][CH:14]([CH2:19][CH:18]2[CH2:17]4)[CH2:13]3)[CH:5]=[CH:6][CH:7]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 21226206Ethyl acetate hexaneHCID 53971236[(3-Hydroxyphenyl)methoxymethylene]adamantane2×

Product 1

HCID 67564241[(3-Acetoxyphenyl)methoxymethylene]adamantane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[(3-Acetoxyphenyl)methoxymethylene]adamantane (1b) was prepared as described in the previous application. Hydroxy alkene 1a (0.75 g, 2.8 mmol) was dissolved in 10 mL of CH2Cl2 and pyridine (5.2 g, 65.8 mmol) under N2. The solution was cooled in an ice bath and a solution of acetyl chloride (2.6 g, 33 mmol) in 1 mL of CH2Cl2 was added dropwise via syringe. After 5 min at 0° C., TLC on silica with 20% ethyl acetate/hexane showed complete acetylation of 1a. After removal of the solvent, the solid residue was washed with 30 mL of ether. The ether was washed with 3×25 mL of water, dried over MgSO4, and evaporated to dryness. The product was chromatographed on silica using 20% ethyl acetate/hexane affording 0.45 g of 1b as an oil: 1H NMR (CDCl3) δ1.79-1.96 (m, 12H), 2.27 (s, 3H), 2.66 (s, 1H), 3.26 (s, 1H), 3.29 (s, 3H), 6.99-7.36 (m, 4H); 13C NMR (CDCl3) δ20.90, 28.13, 30.07, 31.99, 36.99, 38.89, 39.01, 57.59, 120.34, 122.14, 126.55, 128.66, 132.19, 136.90, 142.59, 150.42, 169.04; MS m/e (rel intensity) 312 (100, M), 270 (25), 255 (19.3), 213 (20.7), 163 (12.2), 121 (30.7), 43 (30); IR (neat) 3006, 2925, 2856, 1725, 1600, 1438, 1362, 1218, 1100 cm-1 ; Anal. Calcd. for C20H24O3 : C, 76.92; H, 7.69, Found: C, 76.96; H, 7.85. ##STR22## [(3-(β-D-Galactopyranosyl)phenyl)methoxymethylene]adamantane(1c)

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customAfter removal of the solvent
  3. washthe solid residue was washed with 30 mL of ether
  4. washThe ether was washed with 3×25 mL of water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe product was chromatographed on silica using 20% ethyl acetate/hexane affording 0.45 g of 1b as an oil

Sources & evidence

ORD record
ord-94e9cce5fe984959aeab7ae8aef35908
Source dataset
uspto-grants-1991_11
Patent number
US05068339

Linked notes

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