Hexane → HCID 20373764, compound

HRID 1834660Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]([CH:8]1[CH2:12][CH2:11][CH:10]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:9]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:7].[CH3:29][CH2:30][CH2:31]CCC>C1(C)C=CC=CC=1.CCOCC>[OH:7][CH:6]([CH:8]1[CH2:12][CH2:11][CH:10]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:9]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:4]#[C:3][CH2:2][CH2:1][CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: -70 °C

Procedure

Under a nitrogen atmosphere at -40° C, a solution of 70.4 ml of n-butyl lithium in hexane (2.3 molar) is added dropwise to a solution of 1-heptane (14.78 g, 2.2 equivalents) in 50 ml of toluene. The mixture is stirred at the same temperature for 10 minutes. The solution is transferred carefully to an additional funnel and added at to a solution of 2-formyl-5-(tetrahydropyran-2-yloxy)-cyclopentaneheptanoic acid (22.82 g, 1 equivalent), described in Example 1, in 50 ml of toluene cooled to -70° C. The reaction is stirred at the same temperature for 2 hr. The mixture then is diluted with ether and washed with water. The aqueous layer is acidified with acetic acid and extracted with ether. The ether extract is washed with water, dried and concentrated to give the title compound, nmr (CDCl3) δ 0.89 (t, 3H), 3.90 (broad, 1H), 4.33 (m, 1H).

Workup

customThe solution is transferred carefully to an additional funnel
stirringThe reaction is stirred at the same temperature for 2 hr
washwashed with water
extractionextracted with ether
extractionThe ether extract
washis washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-b7063855d7f14a9a96d6a4a8e670acdf
Source dataset: uspto-grants-1978_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04070482

Reaction notes

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