Acetic Anhydride → HCID 67693742, compound

HRID 1648689Notes

Reaction equation

HRID 1648689 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5](/[C:9](=[CH:12]/[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)/[CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:31]([O:11][CH2:10]/[C:9](/[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:29])([F:30])[F:1])[CH:4]=1)=[CH:12]\[CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 19920698HCID 19920698, compound

Product 1

HCID 67693742HCID 67693742, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of (Z)-2-(3-trifluoromethylphenyl)-5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-pentenol 5r (0.99 g, 2.4 mmol) in anhydrous pyridine (25 mL) at room temperature under argon was treated with 4-dimethylaminopyridine (0.01 g) and acetic anhydride (0.32 g, 3.1 mmol). The reaction mixture was stirred for 2 h and then partitioned between diethyl ether (100 mL) and 1N HCl solution (50 mL). The ether layer was washed further with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 1.09 g (100%) of the product as a colorless oil. The acetate was used without purification in the next reaction. 1H NMR (300 MHz, CDCl3) δ7.50 (d, J=8 Hz, 1H, 2-ArH), 7.36-7.41 (m, 2H, 2-ArH), 7.17 (d, J=8 Hz, 1H, 2-ArH), 7.11 (d, J=8 Hz, 1H, 5-ArH), 6.98 (d, J=2 Hz, 1H, 5-ArH), 6.82 (dd, J=2, 8 Hz, 1 Hz, 5-ArH), 5.89 (t, J=7.5 Hz, 1H, C=CH), 4.73 (s, 2H, CH2OAc), 2.61 (t, J=7 Hz, 2H, ArCH2), 2.24 (q, J=7 Hz, 2H, ArCH2CH2), 1.99 (s, 3H, CH3C=O), 1.64 (s, 4H, CH2CH2), 1.24 (s, 6H, 2'CH3), and 1.22 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ170.66 (C=O), 144.70, 142.52, 138.81, 137.91, 134.89, 133.09, 131.95, 128.67, 126.48, 126.45, 125.73, 125.36, 125.31, 124.02, 68.68 (CH2OAc), 35.33, 35.14, 35.09, 34.12, 31.87, 31.81, 30.67, and 20.89; IR (film) 2960, 2925, 2860, 1745 (C=O), 1325, 1225, 1165, and 1130 cm-1 ; MS (DCI) m/e 399 (M+ --OAc).

Workup

  1. custompartitioned between diethyl ether (100 mL) and 1N HCl solution (50 mL)
  2. washThe ether layer was washed further with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e4253549d516486e8c6029cbeae3f8b1
Source dataset
uspto-grants-1995_07
Patent number
US05436369

Reaction notes

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