3,4-dihydro-2H-pyran → HCID 12042330, compound

HRID 1377835Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][C:7](=[O:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([OH:26])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31](S(O)(=O)=O)=CC=1.[O:39]1[CH:44]=[CH:43][CH2:42][CH2:41][CH2:40]1.C([O-])(O)=[O:46].[Na+]>C(Cl)Cl>[O:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH:44]1[O:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][C:7](=[O:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([O:26][CH:31]1[CH2:32][CH2:33][CH2:28][CH2:38][O:46]1)[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1.2 g (3.2 mmol) of diol 26 and 0.05 g of p-toluenesulfonic acid monohydrate in 100 mL of CH2Cl2 at 0° C. was treated with 3,4-dihydro-2H-pyran (1.1 ml, 12 mmol) and the solution was stirred for 2 h at 0° C. After pouring into saturated NaHCO3, phases were separated and the organic layer was dried over MgSO4, filtered, concentrated, and purified by chromatography on silica gel (1/1, hexanes/EtOAc) to afford 1.1 g of 27 as a clear, colorless oil. 1H NMR (CDCl3) δ 8.04 (dd, J=7.0, 1.6, 1H), 7.44 (m, 2H), 7.12 (m, 1H), 4.95 (dt, 1H), 4.8 (m, 1H), 4.7 (m, 2H), 4.15-3.80 (m, 4H), 3.5 (m, 2H), 2.82 (dd, J=10.8, 1H), 2.55 (m, 2H), 2.3 (m, 1H), 2.1-1.3 (m, 6H).

Workup

customwere separated
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by chromatography on silica gel (1/1, hexanes/EtOAc)

Sources & evidence

ORD record: ord-1009f24d08a8404f934f17c16c5fd39a
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665773

Reaction notes

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