HCID 86706149, compound → HCID 86706156, compound

HRID 2176307Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[C:7]([CH2:12][OH:13])([CH2:10][OH:11])[CH:8]=[CH2:9])(C)(C)[CH3:2].C(OC(C1(C=C)COC(C)(C)OC1)=O)C>>[CH2:1]([O:5][C:6](=[O:14])[C:7]([CH2:10][OH:11])([CH2:12][OH:13])[CH:8]=[CH2:9])[CH3:2]

Participants

Reactant 2

HCID 86706149HCID 86706149, compound

HCID 86706155HCID 86706155, compound

Product 1

HCID 86706156HCID 86706156, compoundYield 78%

Procedure

Compound 99c was prepared in the same manner as 2,2-bis-hydroxymethyl-but-3-enoic acid tert-butyl ester using 2,2-dimethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid ethyl ester instead of 2,2-dimethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid tert-butyl ester in 78% yield. 1H NMR (300 MHz, d6-DMSO) 61.17 (t, J=7.0 Hz, 3H), 3.59-3.71 (m, 4H), 4.06 (q, J=7.0 Hz, 2H), 4.65 (t, J=5.6 Hz, 2H), 5.13 (d, J=18.5 Hz, 1H), 5.15 (d, J=10.5 Hz, 1H), 5.80 (dd, J=18.5, 10.5 Hz, 1H). LCMS (m/z) 197.1 [M+Na], Tr=0.96 min.

Workup

customLCMS (m/z) 197.1 [M+Na], Tr=0.96 min.

Sources & evidence

ORD record: ord-9f15521292d749fb8744d2435f777921
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062092B2

Reaction notes

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