Methyl iodide → Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate

HRID 2168460Notes

Reaction equation

[CH:1](NC(C)C)(C)C.C([Li])CCC.[O:13]1[C:17]2([CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1.CI>O1CCCC1.O>[CH3:1][C:20]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 500 mL round-bottomed flask was added diisopropylamine (7.98 mL) in tetrahydrofuran (233 mL). The mixture was cooled to −78° C. under N2 and n-butyllithium (2.5 M in hexanes, 22.40 mL) was added. The reaction was stirred for 30 minutes and ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (10 g) was added. The reaction was allowed to stir for 1.5 hours upon which time CH3I (4.38 mL) was added. The reaction was allowed to warm to room temperature overnight with stirring. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organics were dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate).

Workup

additionwas added
temperatureto warm to room temperature overnight
stirringwith stirring
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated by rotary evaporation
customThe residue was purified by normal phase flash column chromatography (Analogix, 0-50% hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-bdc4fcd2d44c45939ba2ae3c3025dbd6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045420B2

Reaction notes

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