Ammonia → 6,6-Ethylenedioxy-2-(4'-hydroxybutyl)-2-methyloxepane

HRID 851333Notes

Reaction equation

C(O)(C)(C)C.N.C([O:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1([CH3:30])[CH2:25][CH2:24][CH2:23][C:22]2([O:29][CH2:28][CH2:27][O:26]2)[CH2:21][O:20]1)C1C=CC=CC=1.[Na]>O1CCCC1>[CH2:28]1[CH2:27][O:26][C:22]2([CH2:21][O:20][C:19]([CH2:18][CH2:17][CH2:16][CH2:15][OH:14])([CH3:30])[CH2:25][CH2:24][CH2:23]2)[O:29]1

Participants

Conditions

Temperature: 78 °C

Procedure

t-Butyl alcohol (8.88 g, 0.12 mol) is added to freshly distilled ammonia (360 ml) cooled to 78° C. in an argon atmosphere. The cooling bath is removed and 2-(4'-benzyloxybutyl)-6,6-ethylenedioxy-2-methyloxepane (6.7 g, 0.02 mol) in tetrahydrofuran (90 ml) is added. Freshly cut sodium metal (1.0 g, 0.04 mol) is added in small pieces and the resulting blue solution is stirred for 30 minutes. The reaction is quenched by adding ether (350 ml) followed by water (5 ml). The ammonia is evaporated at room temperature and the ether phase is washed with satd. NaCl (300 ml). The aqueous phase is extracted with ether (5×100 ml). The ether phases are combined, dried (MgSO4) and the solvents are removed under reduced pressure to give 6,6-ethylenedioxy-2-(4'-hydroxybutyl)-2-methyloxepane (13) (4.88 g, 99%): nmr (CDCl3) δ1.18 (s, 3H, CH3), 1.30 (s, 1H, OH), 3.42 (s, 2H, --O--CH2), 3.60 (m, 2H, HO--CH2 --CH2) 3.98 (s, 4H, ketal).

Workup

customThe cooling bath is removed
customThe reaction is quenched
additionby adding ether (350 ml)
customThe ammonia is evaporated at room temperature
washthe ether phase is washed with satd
extractionThe aqueous phase is extracted with ether (5×100 ml)
dry with materialdried (MgSO4)
customthe solvents are removed under reduced pressure

Sources & evidence

ORD record: ord-63aec8079fbf46d0aeb2129c79157ba0
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04384126

Reaction notes

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