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

HRID 1698925Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][C@H:8]([OH:20])[CH2:9][CH2:10][CH:11]1[C:15](=[O:16])O[CH:13]2C[CH2:18][CH2:19][CH:12]12.[OH2:26].[C:27]1(C)C=[CH:31][C:30](S(O)(=O)=O)=[CH:29][CH:28]=1.[O:38]1[CH:43]=[CH:42][CH2:41][CH2:40][CH2:39]1.[C:44]([O-:47])([OH:46])=O.[Na+]>C(Cl)Cl>[O:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH:43]1[O:16][C@@H:15]1[CH2:18][C@@H:19]2[O:46][C:44](=[O:47])[CH2:13][C@@H:12]2[C@H:11]1[CH2:10][CH2:9][C@@H:8]([O:20][CH:31]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH2:7][O:6][C:5]1[CH:21]=[CH:22][CH:23]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=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, 1 H), 7.44 (m, 2 H), 7.12 (m, 1 H), 4.95 (dt, 1 H), 4.8 (m, 1 H), 4.7 (m, 2 H), 4.15-3.80 (m, 4 H), 3.5 (m, 2 H), 2.82 (dd, J=10.8, 1 H), 2.55 (m, 2 H), 2.3 (m, 1 H), 2.1-1.3 (m, 6 H).

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-2c0e729ec6994091bd3f1332cceb626c
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344478B2

Reaction notes

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