Phenylacetyl chloride → 5,6-Dihydro-4-hydroxy-6,6-diphenyl-3-(3-phenylpropyl)-2H-pyran-2-one

HRID 481877Notes

Reaction equation

HRID 481877 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:5][C:4](=[O:20])[CH:3]=1.[C:21]1([CH2:27][C:28](Cl)=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:31](N(CC)CC)C.C1COCC1>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][C:4](=[O:20])[C:3]=1[CH2:31][CH2:28][CH2:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 546804105,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 547140685,6-Dihydro-4-hydroxy-6,6-diphenyl-3-(3-phenylpropyl)-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared as described in General Method 5 using 2.5 mmol of 5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one, 2.7 mmol of phenylacetyl chloride, 2.8 mmol of triethylamine, and 20 mL of THF, followed by 20 mL of toluene and catalytic DMAP. Chromatography of the residue afforded 1.0 mmol of the intermediate 3-acyl compound. Reduction of this acyl derivative was accomplished with 3 mmol of sodium cyanoborohydride. The product was triturated from ether to give the title compound (m.p. 61°-63° C.). 1H NMR (DMSO-d6) δ1.35 (m, 2H), 2.05 (t, 2H), 2.14 (t, 2H), 3.42 (bs, 2H), 6.92 (m, 2H), 7.17-7.40 (m, 13H).

Sources & evidence

ORD record
ord-04c221963fca487bb6d8c38561edb8d4
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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