Ethyl (+/-)-3-[4-(2-tetrahydropyranyloxy)-1-butyn-1-yl]-5H-dibenzo[a,d]cycloheptene-10-acetate → ethyl (+/-)-3-[4-(2-tetrahydropyranyloxy)-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetate

HRID 613385Notes

Reaction equation

HRID 613385 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:21]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1>[Pd].CCOC(C)=O>[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[CH:13]=[CH:14][C:15]2[CH:21]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

4

Reactant 1

HCID 86754984Ethyl (+/-)-3-[4-(2-tetrahydropyranyloxy)-1-butyn-1-yl]-5H-dibenzo[a,d]cycloheptene-10-acetate

Product 1

HCID 54150655ethyl (+/-)-3-[4-(2-tetrahydropyranyloxy)-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetateYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl (±)-3-[4-(2-tetrahydropyranyloxy)-1-butyn-1-yl]-5H-dibenzo[a,d]cycloheptene-10-acetate (1.2 g, 2.77 mmole), 10% Pd/C (0.3 g, 0.28 mmole), and EtOAc (28 mL) was shaken at RT under hydrogen (50 psi) on a Parr apparatus. After 3 hr, the reaction was filtered through celite® and the filtrate was concentrated. Silica gel chromatography (10% EtOAc/hexanes) gave the title compound (1.06 g, 88%) as a colorless oil: TLC (20% EtOAc/hexanes) Rf 0.51; 1H NMR (400 MHz, CDCl3) δ 7.05-7.20 (m, 4 H), 6.92-7.03 (m, 3 H), 4.53-4.60 (m, 1 H), 4.34 (d, J=15.1 Hz, 1 Hz, 1 H), 4.12-4.26 (m, 2 H), 3.80-3.90 (m, 3 H), 3.71-3.80 (m, 1 H), 3.44-3.53 (m, 1 H), 3.35-3.44 (m, 1 H), 3.33 (dd, J=15.1, 4.1 Hz, 1 H), 2.95 (dd, J=15.1, 9.4 Hz, 1 H), 2.65 (dd, J=15.5, 4.9 Hz, 1 H), 2.49-2.61 (m, 3 H), 1.77-1.90 (m, 1 H), 1.45-1.77 (m, 9 H), 1.27 (t, J=7.1 Hz, 3 H); MS (ES) m/e 459 (M+Na)+.

Workup

  1. filtrationthe reaction was filtered through celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-926471188537441a9e36ad9f7ebc82cd
Source dataset
uspto-grants-1999_12
Patent number
US06008213

Reaction notes

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