Propionic Acid → HCID 53657678, compound

HRID 1781543Notes

Reaction equation

C(O)(=O)CC.[Si:6]([O:13][C:14]1[C:22]([CH2:23][CH:24](O)[C:25]([CH3:27])=[CH2:26])=[C:21]([O:29][CH3:30])[C:20]([CH3:31])=[C:19]2[C:15]=1[C:16](=[O:32])[O:17][CH2:18]2)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH3:33][O:34][C:35](OC)([O:40]C)[CH2:36][CH2:37][CH2:38][Br:39]>>[Br:39][CH2:38][CH2:37][CH:36]([CH2:26][C:25]([CH3:27])=[CH:24][CH2:23][C:22]1[C:14]([O:13][Si:6]([C:9]([CH3:11])([CH3:12])[CH3:10])([CH3:7])[CH3:8])=[C:15]2[C:19](=[C:20]([CH3:31])[C:21]=1[O:29][CH3:30])[CH2:18][O:17][C:16]2=[O:32])[C:35]([O:34][CH3:33])=[O:40]

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 5187924Trimethyl 4-bromoorthobutyrate

HCID 10069108HCID 10069108, compound

Product 1

HCID 53657678HCID 53657678, compound

Procedure

A solution of trimethyl 4-bromoorthobutyrate (20 ml), propionic acid (0.22 ml) and 4-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-2-methylbut-1-ene (3.18 g) was heated at 110° C. in a three-necked flash with a slow nitrogen stream passing over the reaction mixture. After 1 hr 40 min the excess orthoester was removed in vacuo at 55° C. Flash chromatography of the residue on silica gel eluting with 20-30% ethyl acetate/hexane gave methyl 2-(2-bromoethyl) -6-(4-t -butyldimethylsiloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran -5-yl)-4-methyl-hex-4-enoate (2.66 g ).

Workup

customAfter 1 hr 40 min the excess orthoester was removed in vacuo at 55° C

Sources & evidence

ORD record: ord-a0f89bc489b2437c8013eb1e5e984063
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05633279

Reaction notes

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