Benzene → HCID 24879670, compound

HRID 1468733Notes

Reaction equation

HRID 1468733 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[C:10]([OH:20])([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:11][C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[OH:20][C@:10]([CH2:15][CH:16]=[C:17]([CH3:18])[CH3:19])([CH2:11][C:12]([O:14][CH3:22])=[O:13])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:21]

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 67043395HCID 67043395, compound

Product 1

HCID 24879670HCID 24879670, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acid 75 (175.2 mg, 0.599 mmol, 1.00 equiv) in 7:2 PhH:MeOH (6.0 mL) was added a 2.0 M solution of TMSCHN2 (449 μL, 0.899 mmol, 1.50 equiv.). After the resulting gas evolution had subsided, the solvent was removed by rotary evaporation to yield methyl ester 77 (183.7 mg, 100%) as a clear, colorless oil. Rf=0.55 (2:1 hex:EtOAc); 1H NMR (500 MHz, CDCl3) δ 7.36 (m, 5H, aryl H), 5.23 (d, 1H, J=12.1 Hz, PhCH2), 5.19 (d, 1H, J=12.1 Hz, PhCH2), 5.08 (m, 1H, vinyl H), 3.68 (s, 1H, OH), 3.62 (s, 3H, OCH3), 2.95 (d, 1H, J=16.2 Hz, C(O)CH2), 2.72 (d, 1H, J=16.3 Hz, C(O)CH2), 2.41 (m, 2H, CHCH2), 1.67 (s, 3H, C(CH3)2), 1.54 (s, 3H, C(CH3)2); 13C NMR (125 MHz, CDCl3) δ 174.84, 171.43, 136.54, 135.46, 128.70, 128.66, 128.60, 116.75, 75.65, 67.79, 51.93, 42.81, 38.11, 26.06, 18.09; IR (neat film) 3514 (m), 3034 (w), 2955 (m), 1742 (s), 1498 (w), 1439 (s), 753 (m), 699 (m) cm−1; LRMS (ESI) calc'd for C17H22O5Na (M+Na+) 329.2, found 329.1.

Workup

  1. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-55ab644663f442108fd00d5a686c786a
Source dataset
uspto-grants-2015_04
Patent number
US09006231B2

Reaction notes

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