Ethyl Acetate → HCID 18367354, compound

HRID 380120Notes

Reaction equation

HRID 380120 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).

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-61378b329aee41388a6b4bf053a973fb
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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