Acetic Anhydride → HCID 53907572, compound

HRID 1461399Notes

Reaction equation

HRID 1461399 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13]=1[CH3:22].[C:23](OC(=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:23]([O:21][CH2:20][CH2:19][CH2:18][CH:14]1[CH2:15][CH2:16][CH2:17][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[C:13]1[CH3:22])(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 53834536HCID 53834536, compound

Product 1

HCID 53907572HCID 53907572, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8.2 g (25.6 mmole) of [R-(R*,S*)]-3-[4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl]-2-methyl-2-cyclohexene-1-propanol in 30 ml of dry pyridine at 0° C. was added slowly 4.8 ml (51.3 mmole) of acetic anhydride followed by a catalytic amount of 4-dimethylaminopyridine. The solution was stirred at 0° C. for 3 hours and then quenched with iced water. The mixture was extracted with 3×150 ml of CH2Cl2. The organic extracts were acidified with 1N H2SO4, washed with sat'd NaHCO3, dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column (5:1, hexane/EtOAc), to give 7.3 g (81%) of [R-(R*,S*)]-3-[4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl]-2-methyl-2-cyclohexene-1-propanol acetate as an oil. [α]D25 =-11.09° (CHCl3 c=1.28). IR (CHCl3): 1730 cm-1. 1H NMR (200 MHz): δ1.25 (m, 1H), 1.60-1.72 (m, 18H), 1.61 (s, 3H), 1.80-2.05 (m, 4H), 2.05 (s, 3H), 3.38 (m, 1H), 3.50 (m, 1H), 3.72 (m, 1H), 3.88 (m, 1H), 4.05 (m, 2H), 4.58 (t, J=2.6 Hz, 1H). Mass Spectrum: M+ (352). Anal. for C21H36O4 : Calc. for C, 71.55; H, 10.29. Found: C, 71.16; H, 10.41.

Workup

  1. customquenched with iced water
  2. extractionThe mixture was extracted with 3×150 ml of CH2Cl2
  3. washwashed with sat'd NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column (5:1, hexane/EtOAc)

Sources & evidence

ORD record
ord-4fc45a90c51345a39576d7f0f3863159
Source dataset
uspto-grants-1991_12
Patent number
US05075327

Reaction notes

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