Ethyl Acetate → HCID 18367354, compound

HRID 1741386Notes

Reaction equation

HRID 1741386 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:18]([OH:51])[CH:19]([C:23]3[C:32]4[C:27](=[C:28]([O:33][Si:34]([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH:24]=3)[CH2:20][CH2:21]O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(OCC)(=O)C>O1CCCC1.O>[C:1]1([C:7]2[N:8]=[C:9]([CH:18]3[CH:19]([C:23]4[C:32]5[C:27](=[C:28]([O:33][Si:34]([C:47]([CH3:48])([CH3:50])[CH3:49])([C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=6)[C:41]6[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=6)[CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25][CH:24]=4)[CH2:20][CH2:21][O:51]3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18367359HCID 18367359, compound

Product 1

HCID 18367354HCID 18367354, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4,5-diphenyloxazol-2-yl)-2-hydroxy-1-(2-hydroxyethyl)ethyl]-5-tert-butyldiphenylsilyloxy-3,4-dihydronaphthalene (1.5 g) in tetrahydrofuran (30 ml) were added triphenylphosphine (1.8 g) and diethyl azodiformate (1.2 ml) at room temperature. After being stirred for 12 hours at the same temperature, the mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[2-(4,5-diphenyloxazol-2-yl)tetrahydrofuran-3-yl]-5-tert-butyldiphenylsilyloxy-3,4-dihydronaphthalene (1.0 g). MS (m/z): 674 (M+ +1) IR (Neat): 1580 cm-1NMR (CDCl3, δ): 1.07 (9H, s), 2.0-2.4 (3H, m), 2.6-3.1 (2H, m), 3.8-4.5 (4H, m), 5.47 (1H, d, J=8.0 Hz), 5.93 (1H, m), 6.39 (1H, d, J=8.0 Hz), 6.82 (1H, t, J=8.0 Hz), 7.02 (1H, d, J=8 Hz), 7.2-7.8 (10H, m)

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ef10db72c15241baa945750890dcfeb5
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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