Diiodomethane → HCID 69921920, compound

HRID 2085604Notes

Reaction equation

HRID 2085604 reaction equation
[CH2:1]([Zn]CC)C.COCCOC.ICI.[OH:15][CH2:16]/[CH:17]=[C:18](\[C:20]1[CH:21]=[C:22]([CH2:31][CH2:32][C:33](=[O:38])[CH2:34][CH2:35][CH2:36][CH3:37])[C:23]2[O:27][CH2:26][C:25]([CH3:29])([CH3:28])[C:24]=2[CH:30]=1)/[CH3:19]>ClCCl.CCCCCC.C(OCC)(=O)C>[OH:15][CH2:16][C@H:17]1[CH2:19][C@@:18]1([C:20]1[CH:21]=[C:22]([CH2:31][CH2:32][C:33](=[O:38])[CH2:34][CH2:35][CH2:36][CH3:37])[C:23]2[O:27][CH2:26][C:25]([CH3:29])([CH3:28])[C:24]=2[CH:30]=1)[CH3:1]

Participants

8

Reactant 4

HCID 6346DiiodomethaneHCID 80711,2-DimethoxyethaneHCID 69887471HCID 69887471, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 69921920HCID 69921920, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following General Procedure C and using 1.57M diethylzinc in anhydrous dichloromethane (10 mL, 15.7 mmol), 1,2-dimethoxyethane (1.63 mL, 15.7 mmol), diiodomethane (2.53 mL, 31.4 mmol), 1-[5-((Z)-3-hydroxy-1-methyl-propenyl)-3,3-dimethyl-2,3-dihydro-benzofuran-7-yl]-heptan-3-one (Intermediate 800.18 g, 0.55 mmol), 4A° molecular sieves powder (0.4 g) and (4S-trans)-2-butyl-N,N,N′,N′-tetramethyl[1,3,2]dioxaborolane-[4,5]dicarboxamide (0.34 g, 1.17 mmol) in 3 mL of anhydrous dichloromethane followed by flash column chromatography using 20% ethyl acetate in hexane, the title compound was obtained as a brown oil (0.16 g,85%). It was used as such for the next step.

Sources & evidence

ORD record
ord-1c8baf9d64494051b26e8decbbde8f58
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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