HCID 86706150, compound → HCID 86706155, compound

HRID 2176306Notes

Reaction equation

HRID 2176306 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH:16]=[CH2:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].C(OC(C1(C(=O)C)COC(C)(C)OC1)=O)C>>[CH2:1]([O:5][C:6]([C:8]1([CH:16]=[CH2:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)=[O:7])[CH3:2]

Participants

3

Reactant 2

HCID 86706150HCID 86706150, compoundHCID 86706154HCID 86706154, compound

Product 1

HCID 86706155HCID 86706155, compoundYield 50%

Procedure

Compound 99b was prepared in the same manner as 2,2-dimethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid tert-butyl ester using 5-acetyl-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester instead of 5-acetyl-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid tert-butyl ester in 50% yield over 2 steps. 1H NMR (300 MHz, CDCl3) δ 1.31 (t, J=7.1 Hz, 3H), 1.41 (s, 3H), 1.46 (s, 3H), 4.10 (ABq, ΔδAB=0.44, JAB=11.9 Hz, 4H), 4.26 (q, J=7.1 Hz, 2H), 5.24 (d, J=17.4 Hz, 1H), 5.28 (d, J=10.9 Hz, 1H), 5.24 (dd, J=17.4, 10.9 Hz, 1H). LCMS (m/z) 237.0 [M+Na], Tr=2.14 min.

Workup

  1. customLCMS (m/z) 237.0 [M+Na], Tr=2.14 min.

Sources & evidence

ORD record
ord-c7a04a6cca9243db96443bd66b487931
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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