Estrone → Estrone THP Ether

HRID 651372Notes

Reaction equation

HRID 651372 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[CH2:21]1[CH2:26][O:25][CH:24]=[CH:23][CH2:22]1>>[O:25]1[CH2:26][CH2:21][CH2:22][CH2:23][CH:24]1[O:20][C:9]1[CH:8]=[CH:7][C:6]2[C@@H:5]3[C@H:14]([C@H:15]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 5870EstroneHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 10405885Estrone THP Ether

Procedure

The THP ether 60, which was prepared from estrone 1 (6.3 g, 23.3 mmol) and DHP (3.0 g, 33 mmol) using the same procedure as described for compound 35, was obtained as a white solid (7.5 g, 91%): 1H NMR (300 MHz, CDCl3) δ0.91 (s, 3, CH3), 2.89 (m, 2), 3.60 (m. 1), 3.92 (m, 1), 5.40 (m, 1), 6.81 (d, J=2.5 Hz, 1, ArH), 6.86 (dd, J=2.5, 8.5 Hz, 1, ArH), 7.20 (d, J=8.5 Hz, 1, ArH).

Sources & evidence

ORD record
ord-e9a8134d776e4f1bad2d4e2d1dc734d8
Source dataset
uspto-grants-2001_08
Patent number
US06281205B1

Reaction notes

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