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Tetrahydrofuran → 5,6-Dihydro-4-hydroxy-6-phenyl-3,6-bis(2-phenylethyl)-2H-pyran-2-one

HRID 357849
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HRID 357849 반응식
[OH:1][C:2]1[CH2:7][C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[CH:3]=1.C(Cl)(=O)[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(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:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:5][C:4](=[O:22])[C:3]=1[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
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참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 546823015,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

생성물 1

HCID 547215945,6-Dihydro-4-hydroxy-6-phenyl-3,6-bis(2-phenylethyl)-2H-pyran-2-one

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 1140Toluene용매

실험 절차

The title compound was prepared as described in General Method 5 using 3.0 mmol of 5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one, 3.2 mmol of hydrocinnamoyl chloride, 3.2 mmol of triethylamine, and 30 mL of THF, followed by 30 mL of toluene and catalytic DMAP. Chromatography of the residue afforded 1.5 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:hexane (1:5) to give the title compound (m.p. 68°-70° C.). 1H NMR (DMSO-d6) 2.20 (m, 2 H), 2.35 (m, 2 H), 2.42-2.59 (m, 4 H plus DMSO), 3.06 (q, 2 H), 7.00 (dd, 2 H), 7.07-7.43 (m, 13 H).

출처 및 근거

ORD 기록
ord-102c298bfc51454a8db6318fe9bb13a9
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05840751

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